Details of the Drug

General Information of Drug (ID: DMX0E5B)

Drug Name
Bimatoprost
Synonyms Bimatoprost (topical, alopecia)
Indication
Disease Entry ICD 11 Status REF
Alopecia ED70 Approved [1]
Hypertrichosis of eyelid N.A. Approved [2]
Ocular hypertension 9C61.01 Approved [2]
Glaucoma/ocular hypertension 9C61 Phase 3 [3]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 415.6
Logarithm of the Partition Coefficient (xlogp) 2.8
Rotatable Bond Count (rotbonds) 12
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 0.08 mcg/L [4]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [5]
Clearance
The clearance of drug is 1.5 L/h/kg in healthy subjects [4]
Elimination
67% of the administered dose was found to be excreted in the urine while 25% of the dose was recovered in the feces [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 45 minutes [4]
Metabolism
The drug is metabolized via the hydrolyzed to its active form bimatoprost acid in the eye [6]
Unbound Fraction
The unbound fraction of drug in plasma is 0.12% [7]
Vd
The volume of distribution (Vd) of drug is 0.67 L/kg [8]
Water Solubility
The ability of drug to dissolve in water is measured as 0.8 mg/mL [5]
Chemical Identifiers
Formula
C25H37NO4
IUPAC Name
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
Canonical SMILES
CCNC(=O)CCC/C=C\\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O
InChI
InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1
InChIKey
AQOKCDNYWBIDND-FTOWTWDKSA-N
Cross-matching ID
PubChem CID
5311027
ChEBI ID
CHEBI:51230
CAS Number
155206-00-1
DrugBank ID
DB00905
TTD ID
D0Q2XF
INTEDE ID
DR0213
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin receptor (PTGR) TT9B4N3 NOUNIPROTAC Modulator [9]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [10]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1958).
2 Bimatoprost FDA Label
3 ClinicalTrials.gov (NCT02250651) Safety and Efficacy of Bimatoprost Sustained-Release (SR) in Patients With Open-Angle Glaucoma or Ocular Hypertension. U.S. National Institutes of Health.
4 FDA Approved Drug Products: Lumigan (bimatoprost) ophthalmic solution
5 BDDCS applied to over 900 drugs
6 Bimataprost metabolism, MDPI
7 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
8 Bitamaprost MedSafe NZ
9 Bimatoprost-induced calcium signaling in human T-cells does not involve prostanoid FP or TP receptors. Curr Eye Res. 2009 Mar;34(3):184-95.
10 Product monograph: LUMIGAN RC (Bimatoprost).