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], [2]
Glaucoma/ocular hypertension	9C61	Phase 3	[3]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 415.6
  Topological Polar Surface Area (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

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]

References

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• [2] ClinicalTrials.gov (NCT01387906) Latisse (Bimatoprost .03% Opthalmic Solution) for the Treatment of Hypotrichosis of the Eyebrows: Latisse Versus Placebo. U.S. National Institutes of Health.
• [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
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