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]
Affected Organisms
Humans and other mammals
ATC Code
S01EE03: Bimatoprost
S01EE: Prostaglandin analogues
S01E: ANTIGLAUCOMA PREPARATIONS AND MIOTICS
S01: OPHTHALMOLOGICALS
S: SENSORY ORGANS
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
CHEMBL1200963
CAS Number
155206-00-1
UNII
QXS94885MZ
DrugBank ID
DB00905
TTD ID
D0Q2XF
INTEDE ID
DR0213
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
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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).