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
Affected Organisms
Humans and other mammals
ATC Code
: Misoprostol
A02AG: Antacids with antispasmodics
A02A: ANTACIDS
A02: DRUGS FOR ACID RELATED DISORDERS
A: ALIMENTARY TRACT AND METABOLISM
: Misoprostol
A02AH: Antacids with sodium bicarbonate
A02A: ANTACIDS
A02: DRUGS FOR ACID RELATED DISORDERS
A: ALIMENTARY TRACT AND METABOLISM
: Misoprostol
A02AX: Antacids, other combinations
A02A: ANTACIDS
A02: DRUGS FOR ACID RELATED DISORDERS
A: ALIMENTARY TRACT AND METABOLISM
A02BB01: Misoprostol
A02BB: Prostaglandins
A02B: DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
A02: DRUGS FOR ACID RELATED DISORDERS
A: ALIMENTARY TRACT AND METABOLISM
G02AD06: Misoprostol
G02AD: Prostaglandins
G02A: UTEROTONICS
G02: OTHER GYNECOLOGICALS
G: GENITO URINARY SYSTEM AND SEX HORMONES
G02AD06: Misoprostol
G02AD: Prostaglandins
G02A: UTEROTONICS
G02: OTHER GYNECOLOGICALS
G: GENITO URINARY SYSTEM AND SEX HORMONES
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#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
UNII
0E43V0BB57
DrugBank ID
DB00929
TTD ID
D09ANG
ACDINA ID
D00440
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
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 Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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.