Identification

Name
Caspofungin
Accession Number
DB00520
Description

Caspofungin (brand name Cancidas worldwide) is an antifungal drug and the first member of a new drug class called the echinocandins, as coined by Merck & Co., Inc. It is typically administered intravenously. It shows activity against infections with Aspergillus and Candida, and works by inhibiting β(1,3)-D-Glucan of the fungal cell wall.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 1093.331
Monoisotopic: 1092.643062174
Chemical Formula
C52H88N10O15
Synonyms
  • (4R,5S)-5-((2-Aminoethyl)amino)-N(sup 2)-(10,12-dimethyltetradecanoyl)-4-hydroxy-L-ornithyl-L-threonyl-trans-4-hydroxy-L-prolyl-(S)-4-hydroxy-4-(p-hydroxyphenyl)-L-threonyl-threo-3-hydroxy-L-ornithyl-trans-3-hydroxy-L-proline cyclic (6-1)-peptide
  • Caspofungin
  • Caspofungina
External IDs
  • L 743,872
  • L 743872
  • MK 0991

Pharmacology

Indication

For the treatment of esophageal candidiasis and invasive aspergillosis in patients who are refractory to or intolerant of other therapies.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Caspofungin is an antifungal drug, and belongs to a new class termed the echinocandins. It is used to treat Aspergillus and Candida infection, and works by inhibiting cell wall synthesis. Antifungals in the echinocandin class inhibit the synthesis of glucan in the cell wall, probably via the enzyme 1,3-beta glucan synthase. There is a potential for resistance development to occur, however in vitro resistance development to Caspofungin by Aspergillus species has not been studied.

Mechanism of action

Caspofungin inhibits the synthesis of beta-(1,3)-D-glucan, an essential component of the cell wall of Aspergillus species and Candida species. beta-(1,3)-D-glucan is not present in mammalian cells. The primary target is beta-(1,3)-glucan synthase.

TargetActionsOrganism
A1,3-beta-glucan synthase component FKS1
inhibitor
Aspergillus niger (strain CBS 513.88 / FGSC A1513)
Absorption

92% tissue distribution within 36-48 hours after intravenous infusion

Volume of distribution
Not Available
Protein binding

97%

Metabolism

Metabolized slowly by hydrolysis and N-acetylation

Route of elimination

After single intravenous administration of [3H] caspofungin acetate, excretion of caspofungin and its metabolites in humans was 35% of dose in feces and 41% of dose in urine.

Half-life

9-11 hours

Clearance
  • 12 mL/min [After single IV administration]
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Side effects include rash, swelling, and nausea (rare)

Affected organisms
  • Aspergillis, Candida and other fungi
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
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Caspofungin.
AcetylcysteineThe excretion of Caspofungin can be decreased when combined with Acetylcysteine.
AcyclovirThe excretion of Acyclovir can be decreased when combined with Caspofungin.
Adefovir dipivoxilThe excretion of Adefovir dipivoxil can be decreased when combined with Caspofungin.
AlprostadilThe excretion of Alprostadil can be decreased when combined with Caspofungin.
AmbrisentanThe excretion of Ambrisentan can be decreased when combined with Caspofungin.
Aminohippuric acidThe excretion of Caspofungin can be decreased when combined with Aminohippuric acid.
AmprenavirThe excretion of Caspofungin can be decreased when combined with Amprenavir.
ApalutamideThe excretion of Caspofungin can be increased when combined with Apalutamide.
AsunaprevirThe excretion of Asunaprevir can be decreased when combined with Caspofungin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Caspofungin acetateVUW370O5QE179463-17-3OGUJBRYAAJYXQP-IJFZAWIJSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CancidasInjection, powder, lyophilized, for solution7 mg/1mLIntravenousMerck Sharp & Dohme Corp.2001-01-26Not applicableUS flag
CancidasInjection, powder, for solution70 mgIntravenousMerck Sharp & Dohme Limited2001-10-24Not applicableEU flag
CancidasPowder, for solution70 mgIntravenousMerck Ltd.2001-10-23Not applicableCanada flag
CancidasInjection, powder, lyophilized, for solution5 mg/1mLIntravenousMerck Sharp & Dohme Corp.2001-01-26Not applicableUS flag
CancidasInjection, powder, for solution50 mgIntravenousMerck Sharp & Dohme Limited2001-10-24Not applicableEU flag
CancidasPowder, for solution50 mgIntravenousMerck Ltd.2001-08-23Not applicableCanada flag
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousFresenius Kabi USA, LLC2016-12-30Not applicableUS flag
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/1mLIntravenousFresenius Kabi USA, LLC2016-12-30Not applicableUS flag
Caspofungin Acetate for InjectionPowder, for solutionIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Caspofungin Acetate for InjectionPowder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousAlmaject, Inc.2020-03-31Not applicableUS flag
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/1mLIntravenousAlvogen Inc.2017-12-01Not applicableUS flag
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousFosun Pharma USA Inc.2019-04-02Not applicableUS flag
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousSandoz Inc2018-09-04Not applicableUS flag
Caspofungin acetateInjection, powder, for solution7 mg/1mLIntravenousMylan Institutional LLC2017-11-15Not applicableUS flag
Caspofungin AcetateInjection7 mg/1mLIntravenousCipla USA Inc.2018-07-12Not applicableUS flag
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousAlvogen Inc.2017-12-01Not applicableUS flag
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/1mLIntravenousGland Pharma Limited2017-10-29Not applicableUS flag
Caspofungin AcetateInjection, powder, lyophilized, for solution70 mg/10.8mLIntravenousAthenex Pharmaceutical Division, Llc.2017-10-04Not applicableUS flag
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/1mLIntravenousAlmaject, Inc.2020-03-31Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
J02AX04 — Caspofungin
Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
F0XDI6ZL63
CAS number
162808-62-0
InChI Key
JYIKNQVWKBUSNH-WVDDFWQHSA-N
InChI
InChI=1S/C52H88N10O15/c1-5-28(2)24-29(3)12-10-8-6-7-9-11-13-39(69)56-34-26-38(68)46(55-22-21-54)60-50(75)43-37(67)19-23-61(43)52(77)41(36(66)18-20-53)58-49(74)42(45(71)44(70)31-14-16-32(64)17-15-31)59-48(73)35-25-33(65)27-62(35)51(76)40(30(4)63)57-47(34)72/h14-17,28-30,33-38,40-46,55,63-68,70-71H,5-13,18-27,53-54H2,1-4H3,(H,56,69)(H,57,72)(H,58,74)(H,59,73)(H,60,75)/t28-,29+,30+,33+,34-,35-,36+,37-,38+,40-,41-,42-,43-,44-,45-,46-/m0/s1
IUPAC Name
(10R,12S)-N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-3-[(1R)-3-amino-1-hydroxypropyl]-21-[(2-aminoethyl)amino]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,25-trihydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^{9,13}]heptacosan-18-yl]-10,12-dimethyltetradecanamide
SMILES

References

Synthesis Reference

Johannes Ludescher, Ingolf Macher, Ole Storm, Stephan Bertel, "Process and Intermediates for the Synthesis of Caspofungin." U.S. Patent US20080319162, issued December 25, 2008.

US20080319162
General References
  1. Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. doi: 10.1345/aph.1M237. Epub 2009 Sep 1. [PubMed:19724014]
  2. Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [PubMed:16207161]
  3. McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [PubMed:16162025]
  4. Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. [PubMed:16960253]
  5. Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. [PubMed:16990627]
KEGG Drug
D07626
PubChem Compound
3035406
PubChem Substance
46508288
ChemSpider
17277006
RxNav
140108
ChEBI
474180
ChEMBL
CHEMBL499808
Therapeutic Targets Database
DAP000547
PharmGKB
PA164743013
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Caspofungin
AHFS Codes
  • 08:14.16 — Echinocandins
FDA label
Download (87.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableBMI >30 kg/m2 / Infections, Fungal1
4CompletedOtherBacterial Infections and Mycoses / Liver Diseases1
4CompletedPreventionCandidiasis, Invasive1
4CompletedTreatmentCandidemia1
4CompletedTreatmentCritically-ill Patients / Suspected Invasive Candidiasis1
4CompletedTreatmentInvasive Aspergillosis1
4CompletedTreatmentPeritonitis / Shock, Septic1
4RecruitingTreatmentPneumocystis Jirovecii Pneumonia1
4TerminatedTreatmentNeoplasms, Hematologic1
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD) / Pulmonary Invasive Aspergillosis1

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
  • Cardinal Health
  • Merck & Co.
  • Oso Biopharmaceuticals Manufacturing LLC
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous75 mg
InjectionIntravenous50 mg
InjectionIntravenous70 mg
Injection, powder, for solutionIntravenous50 mg
Injection, powder, for solutionIntravenous70 mg
Injection, powder, for solutionIntravenous; Parenteral50 MG
Injection, powder, for solutionIntravenous; Parenteral70 MG
Injection, powder, lyophilized, for solutionNot applicable1 kg/1kg
Injection, solution, concentrateIntravenous50 mg
Injection, solution, concentrateIntravenous70 mg
Powder, for solutionIntravenous50 MG
Powder, for solutionIntravenous70 mg
Injection, powder, lyophilized, for solutionIntravenous50 mg
InjectionIntravenous5 mg/1mL
InjectionIntravenous7 mg/1mL
Injection, powder, for solutionIntravenous5 mg/1mL
Injection, powder, for solutionIntravenous7 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous5 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous50 mg/10.8mL
Injection, powder, lyophilized, for solutionIntravenous7 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous70 mg/10.8mL
Powder, for solutionIntravenous
Injection, powder, for solutionParenteral50 MG
Injection, powder, for solutionParenteral70 MG
Injection, solutionIntravenous50 mg
Injection, solutionIntravenous70 mg
Injection, powder, lyophilized, for solutionIntravenous70 mg
Injection, powder, for solutionIntravenous55.49 mg
Injection, powder, for solutionIntravenous77.69 mg
Prices
Unit descriptionCostUnit
Cancidas iv 70 mg vial421.06USD vial
Cancidas iv 50 mg vial405.25USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5378804No1995-01-032013-03-16US flag
CA2251928No2003-06-172017-04-15Canada flag
CA2118757No2002-05-142014-03-10Canada flag
US6136783Yes2000-10-242017-09-28US flag
US5952300Yes1999-09-142017-09-28US flag
US5514650Yes1996-05-072015-07-26US flag
US9636407No2017-05-022032-12-21US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.367 mg/mLALOGPS
logP0.17ALOGPS
logP-4.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.75ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area412.03 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity278.78 m3·mol-1ChemAxon
Polarizability117.66 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7566
Blood Brain Barrier-0.96
Caco-2 permeable-0.8091
P-glycoprotein substrateSubstrate0.8694
P-glycoprotein inhibitor INon-inhibitor0.9653
P-glycoprotein inhibitor IINon-inhibitor0.9174
Renal organic cation transporterNon-inhibitor0.9379
CYP450 2C9 substrateNon-substrate0.831
CYP450 2D6 substrateNon-substrate0.8166
CYP450 3A4 substrateNon-substrate0.51
CYP450 1A2 substrateNon-inhibitor0.9389
CYP450 2C9 inhibitorNon-inhibitor0.9161
CYP450 2D6 inhibitorNon-inhibitor0.8904
CYP450 2C19 inhibitorNon-inhibitor0.875
CYP450 3A4 inhibitorNon-inhibitor0.9682
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9781
Ames testNon AMES toxic0.7398
CarcinogenicityNon-carcinogens0.8315
BiodegradationNot ready biodegradable0.9683
Rat acute toxicity2.9344 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9637
hERG inhibition (predictor II)Non-inhibitor0.716
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Aspergillus niger (strain CBS 513.88 / FGSC A1513)
Pharmacological action
Yes
Actions
Inhibitor
General Function
1,3-beta-d-glucan synthase activity
Specific Function
Catalytic subunit of the 1,3-beta-glucan synthase. Synthesizes 1,3-beta-glucan, a major structural component of the cell wall. Involved in cell wall synthesis, maintenance and cell wall remodeling ...
Gene Name
fksA
Uniprot ID
A2QLK4
Uniprot Name
1,3-beta-glucan synthase component FKS1
Molecular Weight
216972.8 Da
References
  1. Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. doi: 10.1345/aph.1M237. Epub 2009 Sep 1. [PubMed:19724014]
  2. Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [PubMed:16207161]
  3. McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [PubMed:16162025]
  4. Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. [PubMed:16960253]
  5. Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. [PubMed:16990627]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
There is conflicting evidence in the literature regarding this enzyme action. The EMA label does not consider Caspofungin a CYP3A4 inhibitor, however another resource considers it an 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. Colburn DE, Giles FJ, Oladovich D, Smith JA: In vitro evaluation of cytochrome P450-mediated drug interactions between cytarabine, idarubicin, itraconazole and caspofungin. Hematology. 2004 Jun;9(3):217-21. doi: 10.1080/10245330410001701585. [PubMed:15204103]
  2. Caspofungin EMA label [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
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. Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [PubMed:15716364]
  2. Lempers VJ, van den Heuvel JJ, Russel FG, Aarnoutse RE, Burger DM, Bruggemann RJ, Koenderink JB: Inhibitory Potential of Antifungal Drugs on ATP-Binding Cassette Transporters P-Glycoprotein, MRP1 to MRP5, BCRP, and BSEP. Antimicrob Agents Chemother. 2016 May 23;60(6):3372-9. doi: 10.1128/AAC.02931-15. Print 2016 Jun. [PubMed:27001813]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [PubMed:15716364]
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. Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [PubMed:15716364]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [PubMed:15716364]

Drug created on June 13, 2005 07:24 / Updated on October 29, 2020 19:25

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