Identification

Summary

Asciminib is an inhibitor of ABL/BCR-ABL1 tyrosine kinase for the treatment of patients with Philadelphia chromosome-positive CML, including those with the T315I mutation.

Brand Names
Scemblix
Generic Name
Asciminib
DrugBank Accession Number
DB12597
Background

Asciminib is a tyrosine kinase inhibitor (TKI) used in the treatment of chronic-phase Philadelphia chromosome-positive chronic myeloid leukemia (Ph+ CML). More specifically, it is an inhibitor of the ABL1 kinase activity of the BCR-ABL1 fusion protein6 which serves as a driver of CML proliferation in most patients with the disease.8 It has also shown benefit in Ph+ CML with the T315I mutation, which produces a mutant BCR-ABL1 which is typically treatment-resistant as compared to wild-type BCR-ABL1.

Existing inhibitors of ABL compete at the ATP binding sites of these proteins and can be classified into those that target the active conformation of the kinase domain (dasatinib, bosutinib) and those that target the inactive kinase domain (imatinib, nilotinib, ponatinib).5 Asciminib is unique in that it acts as an allosteric inhibitor, binding at the myristoyl pocket of the BCR-ABL1 protein and locking it into an inactive conformation.6,3

Asciminib received FDA approval on October 29, 2021 (Scemblix, Novartis AG).7

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 449.84
Monoisotopic: 449.1066235
Chemical Formula
C20H18ClF2N5O3
Synonyms
  • Asciminib
External IDs
  • ABL-001
  • ABL001
  • ABL001-NX
  • NVP-ABL001

Pharmacology

Indication

Asciminib is indicated for the treatment of adult patients with Philadelphia chromosome-positive chronic myeloid leukemia (Ph+ CML) in chronic phase who have been previously treated with ≥2 tyrosine kinase inhibitors.6 It is also indicated in the treatment of Ph+ CML in adult patients with the T315I mutation.6

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Asciminib exerts its therapeutic activity by inhibiting an oncogenic protein responsible for the proliferation of CML. It may be administered orally once or twice a day depending on the condition being treated. By increasing the total daily dose 5-fold as compared to standard therapy (80mg daily vs. 400mg daily), it can be used to treat Ph+ CML with the T315I mutation, a typically treatment-resistant variant of the disease.6

As with many other chemotherapeutic agents, asciminib treatment can result in various forms of myelosuppression, including thrombocytopenia and neutropenia.6 Patients should receive frequent laboratory monitoring throughout therapy and dose adjustments may be required based on the severity of observed effects. Patients may also experience pancreatic and/or cardiovascular toxicity, both of which require frequent monitoring and may require dose adjustments as per prescribing information.6

Mechanism of action

In most patients with chronic myeloid leukemia (CML),8 progression of the disease is driven primarily by a translocation of the Philadelphia chromosome that creates an oncogenic fusion gene, BCR-ABL1, between the BCR and ABL1 genes.4 This fusion gene produces a resultant fusion protein, BCR-ABL1, which exhibits elevated tyrosine kinase and transforming activities that contribute to CML proliferation.5

Asciminib is an allosteric inhibitor of the BCR-ABL1 tyrosine kinase.6 It binds to the myristoyl pocket of the ABL1 portion of the fusion protein and locks it into an inactive conformation, preventing its oncogenic activity.6,3

TargetActionsOrganism
ATyrosine-protein kinase ABL1
inhibitor
allosteric modulator
Humans
Absorption

The median Tmax of asciminib following oral administration is 2.5 hours.6 At a dose of 80mg once daily, the steady-state Cmax and AUCtau were 1781 ng/mL and 15112 ng.h/mL, respectively. At a dose of 40mg twice daily, the steady-state Cmax and AUCtau were 793 ng/mL and 5262 ng.h/mL, respectively. At a dose of 200mg twice daily (for treatment of T315I mutants), the steady-state Cmax and AUCtau were 5642 ng/mL and 37547 ng.h/mL, respectively.6

As compared to the fasted state, the co-administration of asciminib with a high-fat meal decreased the AUC and Cmax by 62% and 68%, respectively, and its co-administration with a low-fat meal decreased the AUC and Cmax by 30% and 35%, respectively.6

Volume of distribution

At steady-state, the apparent volume of distribution of asciminib is 151 L.6

Protein binding

In vitro, asciminib is 97% bound to plasma proteins, although the specific protein(s) to which it binds are unclear.6

Metabolism

Asciminib is negligibly metabolized, with unchanged parent drug comprising the main drug component in plasma (~93%) and following excretion (~57% in feces).6 The main circulating metabolites are M30.5, M44, and M29.5, accounting for approximately 5%, 2%, and 0.4% of the total administered dose, respectively.2 The oxidative metabolism of asciminib is mediated by CYP3A4, and the glucuronidation of asciminib is mediated by UGT2B7 and UGT2B17.6

Route of elimination

Asciminib is eliminated via biliary secretion facilitated by breast cancer-resistant protein (BCRP) transporters.6 Following oral administration, approximately 80% and 11% of an asciminib dose was recovered in the feces and urine, respectively.6 Unchanged parent drug accounted for 57% of drug material recovered in the feces and 2.5% in the urine.6

Half-life

The terminal elimination half-life asciminib is 5.5 hours when administered at 40mg twice daily and 9.0 hours when administered at 200mg twice daily.6

Clearance

The total apparent clearance of asciminib is 6.7 L/h at a total daily dose of 80mg and 4.1 L/h at a dose of 200mg twice daily.6

Adverse Effects
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Toxicity

There are no data regarding overdosage with asciminib. The effects associated with overdosage are likely to be consistent with the adverse effect profile of asciminib, and may therefore include significant hematological abnormalities and/or gastrointestinal effects, amongst others.6

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirThe metabolism of Abacavir can be decreased when combined with Asciminib.
AbametapirThe serum concentration of Asciminib can be increased when it is combined with Abametapir.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Asciminib.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Asciminib.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is combined with Asciminib.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Asciminib.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Asciminib.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Asciminib.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Asciminib.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Asciminib.
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Food Interactions
  • Take on an empty stomach. Avoid food consumption for at least 2 hours before and 1 hour after taking asciminib.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Asciminib hydrochlorideC5U34S9XFV2119669-71-3HGCOOPLEWPBLOY-PFEQFJNWSA-N
International/Other Brands
Scemblix (Novartis AG)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ScemblixTablet, film coated40 mg/1OralNovartis Pharmaceuticals Corporation2021-10-29Not applicableUS flag
ScemblixTablet, film coated20 mg/1OralNovartis Pharmaceuticals Corporation2021-10-29Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Aromatic anilides
Alternative Parents
Pyrazolylpyridines / Nicotinamides / Dialkylarylamines / Phenol ethers / Phenoxy compounds / Aminopyridines and derivatives / Imidolactams / Heteroaromatic compounds / Pyrrolidines / Pyrazoles
show 10 more
Substituents
3-pyrazolylpyridine / Alcohol / Alkyl chloride / Alkyl fluoride / Alkyl halide / Amine / Aminopyridine / Aromatic anilide / Aromatic heteromonocyclic compound / Azacycle
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
L1F3R18W77
CAS number
1492952-76-7
InChI Key
VOVZXURTCKPRDQ-CQSZACIVSA-N
InChI
InChI=1S/C20H18ClF2N5O3/c21-20(22,23)31-15-3-1-13(2-4-15)26-19(30)12-9-16(17-5-7-25-27-17)18(24-10-12)28-8-6-14(29)11-28/h1-5,7,9-10,14,29H,6,8,11H2,(H,25,27)(H,26,30)/t14-/m1/s1
IUPAC Name
N-[4-(chlorodifluoromethoxy)phenyl]-6-[(3R)-3-hydroxypyrrolidin-1-yl]-5-(1H-pyrazol-5-yl)pyridine-3-carboxamide
SMILES
O[C@@H]1CCN(C1)C1=C(C=C(C=N1)C(=O)NC1=CC=C(OC(F)(F)Cl)C=C1)C1=CC=NN1

References

Synthesis Reference

Schoepfer J, Jahnke W, Berellini G, Buonamici S, Cotesta S, Cowan-Jacob SW, Dodd S, Drueckes P, Fabbro D, Gabriel T, Groell JM, Grotzfeld RM, Hassan AQ, Henry C, Iyer V, Jones D, Lombardo F, Loo A, Manley PW, Pelle X, Rummel G, Salem B, Warmuth M, Wylie AA, Zoller T, Marzinzik AL, Furet P: Discovery of Asciminib (ABL001), an Allosteric Inhibitor of the Tyrosine Kinase Activity of BCR-ABL1. J Med Chem. 2018 Sep 27;61(18):8120-8135. doi: 10.1021/acs.jmedchem.8b01040. Epub 2018 Sep 7. [PubMed:30137981]

General References
  1. Schoepfer J, Jahnke W, Berellini G, Buonamici S, Cotesta S, Cowan-Jacob SW, Dodd S, Drueckes P, Fabbro D, Gabriel T, Groell JM, Grotzfeld RM, Hassan AQ, Henry C, Iyer V, Jones D, Lombardo F, Loo A, Manley PW, Pelle X, Rummel G, Salem B, Warmuth M, Wylie AA, Zoller T, Marzinzik AL, Furet P: Discovery of Asciminib (ABL001), an Allosteric Inhibitor of the Tyrosine Kinase Activity of BCR-ABL1. J Med Chem. 2018 Sep 27;61(18):8120-8135. doi: 10.1021/acs.jmedchem.8b01040. Epub 2018 Sep 7. [Article]
  2. Tran P, Hanna I, Eggimann FK, Schoepfer J, Ray T, Zhu B, Wang L, Priess P, Tian X, Hourcade-Potelleret F, Einolf HJ: Disposition of asciminib, a potent BCR-ABL1 tyrosine kinase inhibitor, in healthy male subjects. Xenobiotica. 2020 Feb;50(2):150-169. doi: 10.1080/00498254.2019.1594449. Epub 2019 May 6. [Article]
  3. Hou JZ, Ye JC, Pu JJ, Liu H, Ding W, Zheng H, Liu D: Novel agents and regimens for hematological malignancies: recent updates from 2020 ASH annual meeting. J Hematol Oncol. 2021 Apr 21;14(1):66. doi: 10.1186/s13045-021-01077-3. [Article]
  4. Jones JK, Thompson EM: Allosteric Inhibition of ABL Kinases: Therapeutic Potential in Cancer. Mol Cancer Ther. 2020 Sep;19(9):1763-1769. doi: 10.1158/1535-7163.MCT-20-0069. Epub 2020 Jun 30. [Article]
  5. Khatri A, Wang J, Pendergast AM: Multifunctional Abl kinases in health and disease. J Cell Sci. 2016 Jan 1;129(1):9-16. doi: 10.1242/jcs.175521. [Article]
  6. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
  7. FDA News Release: FDA approves asciminib for Philadelphia chromosome-positive chronic myeloid leukemia [Link]
  8. NIH National Cancer Institute: BCR-ABL fusion gene [Link]
PubChem Compound
72165228
PubChem Substance
347828815
ChemSpider
52085218
RxNav
2584304
ChEMBL
CHEMBL4208229
ZINC
ZINC000150275965
PDBe Ligand
AY7
Wikipedia
Asciminib
PDB Entries
5mo4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Not Yet RecruitingTreatmentAcute Lymphoblastic Leukemia (ALL) / Leukemia Chronic Myelogenous Leukemia (CML)1
3Active Not RecruitingTreatmentLeukemia Chronic Myelogenous Leukemia (CML)1
3RecruitingTreatmentChronic Phase Phase Chronic Myelogenous Leukemia (CML)1
3RecruitingTreatmentLeukemia Chronic Myelogenous Leukemia (CML)1
3RecruitingTreatmentPhiladelphia Chromosome Positive (Ph+) Chronic Myeloid Leukemia (CML)1
2Active Not RecruitingTreatmentChronic Myeloid Leukemia (CML) / CML / Hematologic Diseases / Leukemia Chronic Myelogenous Leukemia (CML)1
2Not Yet RecruitingTreatmentAdult CML / Chronic Myeloid Leukemia (CML) / Myeloid Leukemia, Chronic, Chronic Phase / Myeloid Leukemias1
2RecruitingTreatmentChronic Myeloid Leukemia (CML)1
2RecruitingTreatmentChronic Phase Phase Chronic Myelogenous Leukemia (CML)1
2RecruitingTreatmentLeukemia Chronic Myelogenous Leukemia (CML)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8829195No2013-05-132033-05-13US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0545 mg/mLALOGPS
logP3.08ALOGPS
logP3.4ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)11.06ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.81 m3·mol-1ChemAxon
Polarizability41.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Allosteric modulator
General Function
Syntaxin binding
Specific Function
Non-receptor tyrosine-protein kinase that plays a role in many key processes linked to cell growth and survival such as cytoskeleton remodeling in response to extracellular stimuli, cell motility a...
Gene Name
ABL1
Uniprot ID
P00519
Uniprot Name
Tyrosine-protein kinase ABL1
Molecular Weight
122871.435 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbe...
Gene Name
UGT2B17
Uniprot ID
O75795
Uniprot Name
UDP-glucuronosyltransferase 2B17
Molecular Weight
61094.915 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Asciminib may reversibly inhibit UGT1A1 at plasma concentrations reached at a total daily dose of 80 mg and 200 mg twice daily.
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Asciminib may reversibly inhibit CYP2C19 at concentrations reached at 200 mg twice daily dose.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. FDA Approved Drug Products: Scemblix (asciminib) tablets for oral use [Link]

Drug created at October 20, 2016 23:07 / Updated at November 27, 2021 01:23