Dactinomycin

Identification

Summary

Dactinomycin is an actinomycin used to treat a wide variety of cancers.

Brand Names
Cosmegen
Generic Name
Dactinomycin
DrugBank Accession Number
DB00970
Background

A compound composed of a two cyclic peptides attached to a phenoxazine that is derived from streptomyces parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 1255.417
Monoisotopic: 1254.628474764
Chemical Formula
C62H86N12O16
Synonyms
  • 2-amino-N,N'-bis(hexadecahydro-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxo-1H-pyrrolo(2,1-i)(1,4,7,10,13)oxatetra-azacyclohexadecin-10-yl)-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide
  • 3H-PHENOXAZINE-1,9-DICARBOXAMIDE, 2-AMINO-N,N'-BIS(HEXADECAHYDRO-6,13-DIISOPROPYL-2,5,9-TRIMETHYL-1,4,7,11,14-PENTAOXO-1H-PYRROLO(2,1-I)(1,4,7,10,13)OXATETRAAZACYCLOHEXADECIN-10-YL)-4,6-DIMETHYL-3-OXO-
  • ActD
  • Actinomycin C1
  • Actinomycin D
  • ACTINOMYCIN I1
  • Actinomycin IV
  • ACTINOMYCIN X1
  • ACTINOMYCIN-D
  • ANA-conjugated dactinomycin nanoemulsion
  • Dactinomicina
  • Dactinomycin
  • Dactinomycine
  • Dactinomycinum
  • DILACTONE ACTINOMYCIN D ACID
  • Meractinomycin
  • N,N'-((2-AMINO-4,6-DIMETHYL-3-OXO-3H-PHENOXAZINE-1,9-DIYL)-BIS(CARBONYLIMINO(2-HYDROXYPROPYLIDENE)CARBONYLIMINOISOBUTYLIDENECARBONYL-1,2-PYRROLIDINEDIYLCARBONYL(METHYLIMINO)METHYLENECARBONYL))BIS(N-METHYL-L-VALINE) DILACTONE
  • ONCOSTATIN K
External IDs
  • GNF-PF-2290
  • NCI-C04682
  • NSC-3053

Pharmacology

Indication

For the treatment of Wilms' tumor, childhood rhabdomyosarcoma, Ewing's sarcoma and metastatic, nonseminomatous testicular cancer as part of a combination chemotherapy and/or multi-modality treatment regimen

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatEwing's sarcoma••••••••••••
Used in combination to treatGestational trophoblastic tumor••••••••••••
Used in combination to treatOsteosarcoma••• •••••
Used in combination to treatOvarian cancer••• •••••
Used in combination to treatRhabdomyosarcoma••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Generally, the actinomycins exert an inhibitory effect on gram-positive and gram-negative bacteria and on some fungi. However, the toxic properties of the actinomycins (including dactinomycin) in relation to antibacterial activity are such as to preclude their use as antibiotics in the treatment of infectious diseases. Because the actinomycins are cytotoxic, they have an antineoplastic effect which has been demonstrated in experimental animals with various types of tumor implant. This cytotoxic action is the basis for their use in the treatment of certain types of cancer. Dactinomycin is believed to produce its cytotoxic effects by binding DNA and inhibiting RNA synthesis.

Mechanism of action

Good evidence exists that this drug bind strongly, but reversibly, to DNA, interfering with synthesis of RNA (prevention of RNA polymerase elongation) and, consequently, with protein synthesis.

TargetActionsOrganism
ADNA
adduct
Humans
UDNA topoisomerase 2
inhibitor
Humans
UDNA topoisomerase 1
inhibitor
Humans
Absorption

poorly absorbed from gastrointestinal tract

Volume of distribution

Not Available

Protein binding

5%

Metabolism

hepatic

Route of elimination

Not Available

Half-life

36 hours

Clearance

Not Available

Adverse Effects
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Toxicity

hepatoxicity

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
AbataceptThe risk or severity of adverse effects can be increased when Dactinomycin is combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Dactinomycin.
AbemaciclibAbemaciclib may decrease the excretion rate of Dactinomycin which could result in a higher serum level.
AbrocitinibThe serum concentration of Dactinomycin can be increased when it is combined with Abrocitinib.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Dactinomycin.
Food Interactions
No interactions found.

Products

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International/Other Brands
Lyovac Cosmegen (Lundbeck)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CosmegenPowder, for solution0.5 mg / vialIntravenousRecordati Rare Diseases Canada Inc1963-12-31Not applicableCanada flag
CosmegenInjection, powder, lyophilized, for solution0.5 mg/1mLIntravenousMerck & Co., Inc.2007-01-012008-08-04US flag
CosmegenInjection, powder, lyophilized, for solution0.5 mg/1mLIntravenousRECORDATI RARE DISEASES, INC.1964-12-102024-11-30US flag
CosmegenInjection, powder, lyophilized, for solution0.5 mg/1mLIntravenousLundbeck Inc.1964-12-102013-04-23US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DactinomycinInjection, powder, lyophilized, for solution0.5 mg/1mLIntravenousMeitheal Pharmaceuticals Inc.2020-11-13Not applicableUS flag
DactinomycinInjection, powder, lyophilized, for solution0.5 mg/1mLIntravenousPrasco Laboratories2017-12-042024-11-30US flag
DactinomycinInjection, powder, for solution500 ug/1IntravenousBedford Pharmaceuticals2010-07-122012-05-31US flag
DactinomycinInjection, powder, lyophilized, for solution0.5 mg/1mLIntravenousEugia US LLC2021-03-15Not applicableUS flag
DactinomycinInjection, powder, lyophilized, for solution0.5 mg/1IntravenousHisun Pharmaceuticals Usa, Inc.2021-01-01Not applicableUS flag

Categories

ATC Codes
L01DA01 — Dactinomycin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Depsipeptides
Direct Parent
Cyclic depsipeptides
Alternative Parents
Macrolide lactams / Phenoxazines / Macrolactams / Alpha amino acid esters / N-acyl-alpha amino acids and derivatives / Benzenoids / Dicarboxylic acids and derivatives / Pyrrolidines / Heteroaromatic compounds / Tertiary carboxylic acid amides
show 12 more
Substituents
Alpha-amino acid ester / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
actinomycin (CHEBI:27666)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
1CC1JFE158
CAS number
50-76-0
InChI Key
RJURFGZVJUQBHK-IIXSONLDSA-N
InChI
InChI=1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1
IUPAC Name
N1,N9-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-bis(propan-2-yl)-hexadecahydro-1H-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-2-amino-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide
SMILES
[H][C@@]12CCCN1C(=O)[C@H](NC(=O)[C@@H](NC(=O)C1=C3N=C4C(OC3=C(C)C=C1)=C(C)C(=O)C(N)=C4C(=O)N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@]3([H])CCCN3C(=O)[C@H](NC1=O)C(C)C)[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C2=O)C(C)C

References

Synthesis Reference

Waksman, S.A. and Woodruff, H.B.; US. Patent 2,378,876; June 19,1945; assigned to Merck & Co., Inc.

General References
  1. Sobell HM: Actinomycin and DNA transcription. Proc Natl Acad Sci U S A. 1985 Aug;82(16):5328-31. [Article]
  2. Turan T, Karacay O, Tulunay G, Boran N, Koc S, Bozok S, Kose MF: Results with EMA/CO (etoposide, methotrexate, actinomycin D, cyclophosphamide, vincristine) chemotherapy in gestational trophoblastic neoplasia. Int J Gynecol Cancer. 2006 May-Jun;16(3):1432-8. [Article]
  3. Abd El-Aal HH, Habib EE, Mishrif MM: Wilms' tumor: the experience of the pediatric unit of Kasr El-Aini center of radiation oncology and nuclear medicine (NEMROCK). J Egypt Natl Canc Inst. 2005 Dec;17(4):308-14. [Article]
  4. Khatua S, Nair CN, Ghosh K: Immune-mediated thrombocytopenia following dactinomycin therapy in a child with alveolar rhabdomyosarcoma: the unresolved issues. J Pediatr Hematol Oncol. 2004 Nov;26(11):777-9. [Article]
Human Metabolome Database
HMDB0015105
KEGG Drug
D00214
KEGG Compound
C06770
PubChem Compound
457193
PubChem Substance
46509192
ChemSpider
10482167
BindingDB
43866
RxNav
3100
ChEBI
27666
ChEMBL
CHEMBL1554
Therapeutic Targets Database
DNC000380
PharmGKB
PA151917012
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dactinomycin

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Lundbeck inc
  • Bedford laboratories div ben venue laboratories inc
Packagers
  • Lundbeck Inc.
  • Merck & Co.
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionParenteral0.5 mg
Injection, powder, for solutionParenteral0.5 MG
Injection, powder, lyophilized, for solutionIntravenous0.5 mg/1mL
Powder, for solutionIntravenous0.5 mg / vial
Injection, powder, lyophilized, for solutionIntravenous0.5 mg
Injection, powder, for solutionIntravenous500 ug/1
Injection, powder, lyophilized, for solutionIntravenous0.5 mg/1
Injection, powder, for solutionIntravenous0.5 mg
Injection, powder, lyophilized, for solution0.5 mg/1vial
Prices
Unit descriptionCostUnit
Cosmegen 0.5 mg vial684.36USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)241.5-243 °CNot Available
water solubilitySoluble at 10 °CNot Available
logP1.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 mg/mLALOGPS
logP2.76ALOGPS
logP-0.097Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)10.52Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area355.54 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity326.17 m3·mol-1Chemaxon
Polarizability129.24 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7619
Blood Brain Barrier-0.9659
Caco-2 permeable-0.6568
P-glycoprotein substrateSubstrate0.8368
P-glycoprotein inhibitor INon-inhibitor0.6482
P-glycoprotein inhibitor IINon-inhibitor0.8638
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8589
CYP450 2D6 substrateNon-substrate0.8535
CYP450 3A4 substrateSubstrate0.759
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8614
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9019
BiodegradationNot ready biodegradable0.983
Rat acute toxicity4.3767 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9208
hERG inhibition (predictor II)Non-inhibitor0.5171
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000400-9a5ab0e87709fcfde113
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090050100-ba4189700f46c0bb1466
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05gi-0070500900-714b2b13b3339095158c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9030800200-9340a63f72e268b7a89b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0070910400-fcb70690ab17392fa5ef
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uem-1160100900-c4f21a4f57ab37395156
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-364.01746
predicted
DeepCCS 1.0 (2019)
[M+H]+365.74118
predicted
DeepCCS 1.0 (2019)
[M+Na]+372.08725
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Adduct
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Yang XL, Wang AH: Structural studies of atom-specific anticancer drugs acting on DNA. Pharmacol Ther. 1999 Sep;83(3):181-215. [Article]
  4. Sobell HM: Actinomycin and DNA transcription. Proc Natl Acad Sci U S A. 1985 Aug;82(16):5328-31. [Article]
  5. Hudson JS, Brooks SC, Graves DE: Interactions of actinomycin D with human telomeric G-quadruplex DNA. Biochemistry. 2009 Jun 2;48(21):4440-7. doi: 10.1021/bi900203z. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...

Components:
References
  1. Felix CA, Hosler MR, Winick NJ, Masterson M, Wilson AE, Lange BJ: ALL-1 gene rearrangements in DNA topoisomerase II inhibitor-related leukemia in children. Blood. 1995 Jun 1;85(11):3250-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Poly(a) rna binding
Specific Function
Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a singl...
Gene Name
TOP1
Uniprot ID
P11387
Uniprot Name
DNA topoisomerase 1
Molecular Weight
90725.19 Da
References
  1. Alkorta I, Park C, Kong J, Garbisu C, Alberti M, Pon N, Hearst JE: Rhodobacter capsulatus DNA topoisomerase I purification and characterization. Arch Biochem Biophys. 1999 Feb 1;362(1):123-30. doi: 10.1006/abbi.1998.1023. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [Article]
  2. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [Article]
  3. Ambudkar SV, Lelong IH, Zhang J, Cardarelli CO, Gottesman MM, Pastan I: Partial purification and reconstitution of the human multidrug-resistance pump: characterization of the drug-stimulatable ATP hydrolysis. Proc Natl Acad Sci U S A. 1992 Sep 15;89(18):8472-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Isoform 1: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4...
Gene Name
ABCC6
Uniprot ID
O95255
Uniprot Name
Multidrug resistance-associated protein 6
Molecular Weight
164904.81 Da
References
  1. Belinsky MG, Chen ZS, Shchaveleva I, Zeng H, Kruh GD: Characterization of the drug resistance and transport properties of multidrug resistance protein 6 (MRP6, ABCC6). Cancer Res. 2002 Nov 1;62(21):6172-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Breuninger LM, Paul S, Gaughan K, Miki T, Chan A, Aaronson SA, Kruh GD: Expression of multidrug resistance-associated protein in NIH/3T3 cells confers multidrug resistance associated with increased drug efflux and altered intracellular drug distribution. Cancer Res. 1995 Nov 15;55(22):5342-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Wang X, Furukawa T, Nitanda T, Okamoto M, Sugimoto Y, Akiyama S, Baba M: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol Pharmacol. 2003 Jan;63(1):65-72. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48