Details of the Drug

General Information of Drug (ID: DMHVJFK)

• Drug Name: Misoprostol
• Synonyms: Cytotec; GyMiso; Isprelor; Misopess; Misoprostolum; Misotol; SC 29333; Cytotec (TN); Misoprostolum [INN-Latin]; SC-29333; XP-16J; Misoprostol (JAN/USAN/INN); Methyl (11alpha,13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate; Methyl (+-)-11-alpha,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate; Methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate; (+/-)-15-Deoxy-(16RS)-16-hydroxy-16-methylprostaglandin E1 methyl ester; (11-alpha,13E)-(+-)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid methyl ester

Indication

Disease Entry	ICD 11	Status	REF
Medical abortion	JA00.1Z	Approved	[1]
Postpartum haemorrhage	JA43	Approved	[2]

• Therapeutic Class: Abortifacient Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 382.5
  Logarithm of the Partition Coefficient (xlogp); 3.7
  Rotatable Bond Count (rotbonds); 14
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 5
• ADMET Property:
  Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 2.0192 +/- 0.8032 mcgh/L [3]
  Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 2.6830 +/- 1.2161 mcg/L [3]
  Absorption Tmax: The time to maximum plasma concentration (Tmax) is 0.345 +/- 0.186 h [3]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
  Bioavailability: 80% of drug becomes completely available to its intended biological destination(s) [5]
  Clearance: The total body clearance of drug is 0.286 L/min/kg [6]
  Elimination: As much as 73.2 +/- 4.6% of a radiolabelled oral dose is recovered in the urine [7]
  Half-life: The concentration or amount of drug in body reduced by one-half in 1.0401 +/- 0.5090 hours [3]
  Metabolism: The drug is metabolized via the de-esterified to its active metabolite, misoprostol acid, also known as SC-30695 [7]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.03477 micromolar/kg/day [8]
  Vd: The volume of distribution (Vd) of drug is 13.6 +/- 8.0 L/kg [6]
• Chemical Identifiers:
  Formula: C22H38O5
  IUPAC Name: methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
  Canonical SMILES: CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)OC)O)O
  InChI: InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1
  InChIKey: OJLOPKGSLYJEMD-URPKTTJQSA-N
• Cross-matching ID:
  PubChem CID: 5282381
  ChEBI ID: CHEBI:94387
  CAS Number: 59122-46-2
  DrugBank ID: DB00929
  TTD ID: D09ANG
  ACDINA ID: D00440
• 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
Prostacyclin receptor (PTGIR)	TTOFYT1	PI2R_HUMAN	Antagonist	[9]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Interleukin-23 subunit alpha (IL23A)	OTYO99HC	IL23A_HUMAN	Gene/Protein Processing	[10]

Molecular Expression Atlas of This Drug

• The Studied Disease: Medical abortion
• ICD Disease Classification: JA00.1Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Prostacyclin receptor (PTGIR)	DTT	PTGIR	7.12E-02	-0.13	-0.33

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Crospovidone	E00626	Not Available	Disintegrant
Hypromellose	E00634	Not Available	Coating agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Misoprostol 0.1 mg tablet	0.1 mg	Oral Tablet	Oral
Misoprostol 0.2 mg tablet	0.2 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page 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: 1936).
• [2] Misoprostol FDA Label
• [3] A crossover pharmacokinetic study of misoprostol by the oral, sublingual and buccal routes. Eur J Contracept Reprod Health Care. 2016 Aug;21(4):265-8. doi: 10.3109/13625187.2016.1168799. Epub 2016 Apr 22.
• [4] BDDCS applied to over 900 drugs
• [5] Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
• [6] Foote EF, Lee DR, Karim A, Keane WF, Halstenson CE: Disposition of misoprostol and its active metabolite in patients with normal and impaired renal function. J Clin Pharmacol. 1995 Apr;35(4):384-9.
• [7] Ganther HE: Selenium metabolism, selenoproteins and mechanisms of cancer prevention: complexities with thioredoxin reductase. Carcinogenesis. 1999 Sep;20(9):1657-66.
• [8] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [9] Palmitoylation of the human prostacyclin receptor. Functional implications of palmitoylation and isoprenylation. J Biol Chem. 2003 Feb 28;278(9):6947-58.
• [10] Prostaglandin E2 regulates Th17 cell differentiation and function through cyclic AMP and EP2/EP4 receptor signaling. J Exp Med. 2009 Mar 16;206(3):535-48. doi: 10.1084/jem.20082293. Epub 2009 Mar 9.