Identification

Name
Misoprostol
Accession Number
DB00929  (APRD00037, DB05379)
Type
Small Molecule
Groups
Approved
Description

A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties.

Structure
Thumb
Synonyms
  • Misoprostolum
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CytotecTablet100 ug/1OralPd Rx Pharmaceuticals, Inc.1986-12-27Not applicableUs
CytotecTablet100 ug/1OralCardinal Health1988-12-272015-12-31Us
CytotecTablet200 ug/1OralApotheca, Inc.2010-01-01Not applicableUs
CytotecTablet200 ug/1OralG.D. Searle LLC Division of Pfizer Inc1986-12-27Not applicableUs
CytotecTablet200 ug/1OralA S Medication Solutions1986-12-27Not applicableUs
CytotecTablet100 ug/1OralG.D. Searle LLC Division of Pfizer Inc1986-12-27Not applicableUs
CytotecTablet200 ug/1OralCardinal Health1988-12-272015-12-31Us
CytotecTablet100 ug/1OralPhysicians Total Care, Inc.1996-07-02Not applicableUs
Cytotec 100 McgTablet100 mcgOralPfizer1989-12-312004-07-26Canada
Cytotec 200 McgTablet200 mcgOralPfizer1986-12-312005-08-05Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MisoprostolTablet100 ug/1OralLupin Pharmaceuticals2012-07-25Not applicableUs
MisoprostolTablet200 ug/1Oralbryant ranch prepack2012-07-25Not applicableUs
MisoprostolTablet200 ug/1OralAvera McKennan Hospital2015-04-06Not applicableUs69189 016120180907 15195 12a6vsq
MisoprostolTablet100 ug/1OralGreenstone, Llc2009-12-27Not applicableUs
MisoprostolTablet100 ug/1OralAidarex Pharmaceuticals LLC2012-07-25Not applicableUs
MisoprostolTablet200 ug/1OralUnit Dose Services2013-04-12Not applicableUs
MisoprostolTablet200 ug/1Oralbryant ranch prepack2002-07-10Not applicableUs
MisoprostolTablet200 ug/1OralAmerincan Health Packaging2013-07-08Not applicableUs
MisoprostolTablet100 ug/1OralIVAX Pharmaceuticals, Inc.2002-07-102013-10-31Us
MisoprostolTablet200 ug/1OralApotheca, Inc.2009-12-27Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Act Diclo-misoMisoprostol (200 mcg) + Diclofenac sodium (75 mg)Tablet, delayed releaseOralActavis Pharma Company2013-03-27Not applicableCanada
Act Diclo-misoMisoprostol (200 mcg) + Diclofenac sodium (50 mg)Tablet, delayed releaseOralActavis Pharma Company2013-03-27Not applicableCanada
ArthrotecMisoprostol (200 ug/1) + Diclofenac sodium (75 mg/1)Tablet, film coatedOralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-02-23Not applicableUs
ArthrotecMisoprostol (200 ug/1) + Diclofenac sodium (75 mg/1)Tablet, film coatedOralRebel Distributors1997-12-24Not applicableUs
ArthrotecMisoprostol (200 ug/1) + Diclofenac sodium (50 mg/1)Tablet, film coatedOralG.D. Searle LLC Division of Pfizer Inc1997-12-24Not applicableUs00025 1411 60 nlmimage10 c812e407
ArthrotecMisoprostol (200 ug/1) + Diclofenac sodium (75 mg/1)Tablet, film coatedOralbryant ranch prepack1997-12-24Not applicableUs63629 335920180907 15195 1t8mfmf
ArthrotecMisoprostol (200 ug/1) + Diclofenac sodium (75 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2004-12-28Not applicableUs54868 416520180907 15195 1jambru
ArthrotecMisoprostol (200 ug/1) + Diclofenac sodium (50 mg/1)Tablet, film coatedOralPd Rx Pharmaceuticals, Inc.1997-12-24Not applicableUs
ArthrotecMisoprostol (200 ug/1) + Diclofenac sodium (75 mg/1)Tablet, film coatedOralA-S Medication Solutions1997-12-24Not applicableUs54569 457920180907 15195 1f77log
ArthrotecMisoprostol (200 ug/1) + Diclofenac sodium (75 mg/1)Tablet, film coatedOralStat Rx USA1997-12-24Not applicableUs
International/Other Brands
Isprelor
Categories
UNII
0E43V0BB57
CAS number
59122-46-2
Weight
Average: 382.5341
Monoisotopic: 382.271924326
Chemical Formula
C22H38O5
InChI Key
OJLOPKGSLYJEMD-URPKTTJQSA-N
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
IUPAC Name
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate
SMILES
CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC

Pharmacology

Indication

Indicated for the treatment of ulceration (duodenal, gastric and NSAID induced) and prophylaxis for NSAID induced ulceration. Misoprostol is also indicated for other uses that are not approved in Canada, including the medical termination of an intrauterine pregnancy used alone or in combination with methotrexate,as well as the induction of labour in a selected population of pregnant women with unfavourable cervices. This indication is avoided in women with prior uterine surgery or cesarean surgery due to an increased risk of possible uterine rupture. Misoprostol is also used for the prevention or treatment of serious postpartum hemorrhage.

Associated Conditions
Associated Therapies
Pharmacodynamics

Misoprostol is a prostaglandin E1 (PGE1) analogue used for the treatment and prevention of stomach ulcers. When administered, misoprostol stimulates increased secretion of the protective mucus that lines the gastrointestinal tract and increases mucosal blood flow, thereby increasing mucosal integrity. It is sometimes co-prescribed with non-steroidal anti-inflammatory drugs (NSAIDs) to prevent the occurrence of gastric ulceration, a common adverse effect of the NSAIDs.

Mechanism of action

Misoprostol seems to inhibit gastric acid secretion by a direct action on the parietal cells through binding to the prostaglandin receptor. The activity of this receptor is mediated by G proteins which normally activate adenylate cyclase. The indirect inhibition of adenylate cyclase by Misoprostol may be dependent on guanosine-5’-triphosphate (GTP). The significant cytoprotective actions of misoprostol are related to several mechanisms. These include: 1. Increased secretion of bicarbonate, 2. Considerable decrease in the volume and pepsin content of the gastric secretions, 3. It prevents harmful agents from disrupting the tight junctions between the epithelial cells which stops the subsequent back diffusion of H+ ions into the gastric mucosa, 4. Increased thickness of mucus layer, 5. Enhanced mucosal blood flow as a result of direct vasodilatation, 6. Stabilization of tissue lysozymes/vascular endothelium, 7. Improvement of mucosal regeneration capacity, and 8. Replacement of prostaglandins that have been depleted as a result of various insults to the area. Misoprostol has also been shown to increase the amplitude and frequency of uterine contractions during pregnancy via selective binding to the EP-2/EP-3 prostanoid receptors.

TargetActionsOrganism
AProstaglandin E2 receptor EP3 subtype
agonist
Human
AProstaglandin E2 receptor EP2 subtype
agonist
Human
UProstaglandin E2 receptor EP4 subtype
agonist
Human
Absorption

Misoprostol is extensively absorbed.

Volume of distribution
Not Available
Protein binding

85%

Metabolism

Rapidly de-esterified to misoprostol acid. The de-esterified metabolite undergoes further metabolism by beta and omega oxidation; oxidation is followed by reduction of the ketone to yield prostaglandin F analogs.

Route of elimination

After a single oral dose of misoprostol to nursing mothers, misoprostol acid was excreted in breast milk.

Half life

20-40 minutes

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AlmasilateThe serum concentration of Misoprostol can be decreased when it is combined with Almasilate.
AloglutamolThe serum concentration of Misoprostol can be decreased when it is combined with Aloglutamol.
AluminiumThe serum concentration of Misoprostol can be decreased when it is combined with Aluminium.
Aluminium acetoacetateThe serum concentration of Misoprostol can be decreased when it is combined with Aluminium acetoacetate.
Aluminium glycinateThe serum concentration of Misoprostol can be decreased when it is combined with Aluminium glycinate.
Aluminium phosphateThe serum concentration of Misoprostol can be decreased when it is combined with Aluminium phosphate.
Aluminum hydroxideThe serum concentration of Misoprostol can be decreased when it is combined with Aluminum hydroxide.
Bismuth subnitrateThe serum concentration of Misoprostol can be decreased when it is combined with Bismuth subnitrate.
Calcium CarbonateThe serum concentration of Misoprostol can be decreased when it is combined with Calcium Carbonate.
Calcium silicateThe serum concentration of Misoprostol can be decreased when it is combined with Calcium silicate.
Food Interactions
  • Take with food to decrease the incidence of diarrhea.

References

Synthesis Reference

Salah Ahmed, Raj Mahajan, "Vaginal tablets comprising misoprostol and methods of making and using the same." U.S. Patent US20070071814, issued March 29, 2007.

US20070071814
General References
  1. Costa SH, Vessey MP: Misoprostol and illegal abortion in Rio de Janeiro, Brazil. Lancet. 1993 May 15;341(8855):1258-61. [PubMed:8098402]
  2. Coelho HL, Teixeira AC, Cruz Mde F, Gonzaga SL, Arrais PS, Luchini L, La Vecchia C, Tognoni G: Misoprostol: the experience of women in Fortaleza, Brazil. Contraception. 1994 Feb;49(2):101-10. [PubMed:8143449]
  3. Barbosa RM, Arilha M: The Brazilian experience with Cytotec. Stud Fam Plann. 1993 Jul-Aug;24(4):236-40. [PubMed:8212093]
  4. Rocha J: Brazil investigates drug's possible link with birth defects. BMJ. 1994 Sep 24;309(6957):757-8. [PubMed:7950553]
  5. Gonzalez CH, Vargas FR, Perez AB, Kim CA, Brunoni D, Marques-Dias MJ, Leone CR, Correa Neto J, Llerena Junior JC, de Almeida JC: Limb deficiency with or without Mobius sequence in seven Brazilian children associated with misoprostol use in the first trimester of pregnancy. Am J Med Genet. 1993 Aug 1;47(1):59-64. [PubMed:8368254]
External Links
Human Metabolome Database
HMDB0015064
KEGG Drug
D00419
PubChem Compound
5282381
PubChem Substance
46505041
ChemSpider
4445541
BindingDB
85606
ChEBI
63610
ChEMBL
CHEMBL606
Therapeutic Targets Database
DAP000358
PharmGKB
PA450523
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Misoprostol
ATC Codes
G02AD06 — MisoprostolM01AE56 — Naproxen and misoprostolA02BB01 — Misoprostol
AHFS Codes
  • 56:28.28 — Prostaglandins
FDA label
Download (246 KB)
MSDS
Download (147 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceGynaecological infection1
0Not Yet RecruitingPreventionPrimary Postpartum Haemorrhage1
1CompletedBasic ScienceHypotonic; Labor1
1CompletedPreventionCesarean Section1
1CompletedPreventionPain Prior to IUD Insertion1
1CompletedPreventionPost Partum Hemorrhage1
1CompletedTreatmentArrest of Dilation in Labor1
1CompletedTreatmentIncomplete Abortion1
1CompletedTreatmentInduction of Labour1
1CompletedTreatmentPlacenta, Retained1
1WithdrawnTreatmentSecond Trimester Labor Induction1
1, 2Active Not RecruitingSupportive CareInduction of Labour1
1, 2CompletedPreventionPostpartum Haemorrhage (PPH)1
1, 2Unknown StatusTreatmentFetal Demise / Fetal Membranes, Premature Rupture / Preeclampsia1
2CompletedPreventionCesarean Delivery / Pregnancy1
2CompletedPreventionPostpartum Haemorrhage (PPH)2
2CompletedTreatmentAbortion, Therapeutic1
2CompletedTreatmentCervical Priming1
2CompletedTreatmentCervical Ripening / Premature Births1
2CompletedTreatmentDelivery Uterine1
2CompletedTreatmentFirst Trimester Pregnancy / Surgical Termination of Pregnancy1
2CompletedTreatmentInduction of Labor Affected Fetus / Newborn1
2CompletedTreatmentInduction of Labour1
2CompletedTreatmentLate Second Trimester Termination of Pregnancy1
2CompletedTreatmentMissed Abortion1
2CompletedTreatmentPain1
2CompletedTreatmentPregnancy Termination1
2Not Yet RecruitingPreventionClostridium Difficile1
2Not Yet RecruitingTreatmentLabor; Forced or Induced, Affecting Fetus or Newborn1
2RecruitingNot AvailableInduction of Labour1
2RecruitingTreatmentAbortions spontaneous / Missed Abortion1
2RecruitingTreatmentCervical Ripening1
2RecruitingTreatmentCervical Spasm1
2RecruitingTreatmentMissed Abortion1
2RecruitingTreatmentPain1
2RecruitingTreatmentPlacenta, Retained / Postpartum Haemorrhage (PPH)1
2RecruitingTreatmentPostpartum Haemorrhage (PPH)1
2RecruitingTreatmentInduction of Uterine contractions1
2TerminatedTreatmentIntra-uterine Residua1
2Unknown StatusNot AvailablePregnancy Termination1
2, 3Active Not RecruitingDiagnosticUlcer Hemorrhage1
2, 3CompletedNot AvailableIUD Insertion1
2, 3CompletedPreventionCesarean Section2
2, 3CompletedPreventionNeonatal Outcome1
2, 3CompletedPreventionPostpartum Haemorrhage (PPH)2
2, 3CompletedTreatmentAbortions spontaneous1
2, 3CompletedTreatmentComplete Miscarriage1
2, 3CompletedTreatmentFailed Induction of Labor1
2, 3CompletedTreatmentPregnancy1
2, 3CompletedTreatmentTermed Pregnancy With Indications for Labor Induction1
2, 3RecruitingTreatmentUterine Leiomyomas1
2, 3SuspendedTreatmentMissed Abortion1
2, 3Unknown StatusPreventionBleeding Intraoperative1
2, 3Unknown StatusTreatmentSpontaneous Abortion in First Trimester1
3Active Not RecruitingDiagnosticPregnancy1
3Active Not RecruitingTreatmentPostpartum Haemorrhage (PPH)1
3Active Not RecruitingTreatmentSpontaneous Abortions1
3CompletedNot AvailableCervical Ripening1
3CompletedNot AvailableLabour Pain1
3CompletedHealth Services ResearchInduction of Uterine contractions1
3CompletedPreventionAbortifacient Agents, Nonsteroidal / Incomplete Abortion / Misoprostol / Pregnancy1
3CompletedPreventionAnkylosing Spondylitis (AS) / Osteoarthritis (OA) / Rheumatoid Arthritis1
3CompletedPreventionComplications; Cesarean Section1
3CompletedPreventionLeiomyomas1
3CompletedPreventionPostpartum Haemorrhage (PPH)2
3CompletedPreventionSevere Pre-eclampsia, Postpartum Condition or Complication1
3CompletedTreatmentAbnormal Uterine and Vaginal Bleeding, Unspecified / Infertilities / Recurrent Abortion1
3CompletedTreatmentAnemias / Chronic Arthritis / Haemorrhage / Ischaemic Heart Diseases / Nonvalvular Atrial Fibrillation1
3CompletedTreatmentCervical Ripening1
3CompletedTreatmentEndometrial Biopsy1
3CompletedTreatmentEndometrial Disorder1
3CompletedTreatmentFailed Induction of Labor1
3CompletedTreatmentFetus or Newborn; Effects of Induction of Labor / Prophylaxis of preeclampsia1
3CompletedTreatmentInduction of Labour3
3CompletedTreatmentIntrauterine Fetal Demise1
3CompletedTreatmentMedical Abortion1
3CompletedTreatmentPost Partum Hemorrhage1
3CompletedTreatmentPostpartum Haemorrhage (PPH)1
3CompletedTreatmentPregnancy1
3CompletedTreatmentPregnancy Termination1
3CompletedTreatmentUterine Hemorrhage1
3RecruitingPreventionPost Partum Hemorrhage1
3RecruitingSupportive CareBlood Loss / Myoma;Uterus1
3RecruitingTreatmentFetal Demise1
3RecruitingTreatmentMedical; Abortion, Fetus1
3TerminatedPreventionBlood Loss / Pregnancy termination therapy1
3TerminatedTreatmentGastric Ulcer (GU)1
3TerminatedTreatmentInduction of Labour1
3TerminatedTreatmentPregnancy Termination1
3TerminatedTreatmentInduction of Uterine contractions1
3Unknown StatusPreventionBlood Loss1
3Unknown StatusTreatmentCervical Ripening1
3Unknown StatusTreatmentMedical Abortion1
3Unknown StatusTreatmentMedical Induction of Labor Affecting Fetus1
3WithdrawnPreventionPostpartum Haemorrhage (PPH)1
3WithdrawnTreatmentCervical Ripening / Endometrial Biopsy / Hypermenorrhea1
4Active Not RecruitingTreatmentAbortion Failure1
4CompletedHealth Services ResearchAbortion, Therapeutic1
4CompletedHealth Services ResearchMenstrual Regulation1
4CompletedOtherContraceptive Device; Complications1
4CompletedPreventionHemorrhage1
4CompletedPreventionNSAID-associated Gastroduodenal Injury1
4CompletedPreventionPostpartum Haemorrhage (PPH)4
4CompletedPreventionPostpartum Haemorrhage (PPH) / Intrapartum Haemorrhage1
4CompletedPreventionProstaglandin E2 "Misoprostol" Prior Abdominal Myomectomy / Prostaglandin E2 Misoprostol Prior Abdominal Myomectomy1
4CompletedTreatmentAbortion Seekers1
4CompletedTreatmentAbortion, 3 Months1
4CompletedTreatmentAbortion, Legal1
4CompletedTreatmentAnembryonic Pregnancy / Gestation Abnormality / Intrauterine Fetal Demise Term1
4CompletedTreatmentCervical Ripening / Induction of Uterine contractions1
4CompletedTreatmentCervical Stenosis1
4CompletedTreatmentComplete Uterine Evacuation After Use of Study Drugs1
4CompletedTreatmentComplications, Pregnancy1
4CompletedTreatmentContraception / Hypermenorrhea1
4CompletedTreatmentInduction of Labour / Pregnancy1
4CompletedTreatmentLabor Augmentation1
4CompletedTreatmentMaternal Care for Late Fetal Death / Pregnancy, Cornual1
4CompletedTreatmentMedical Abortion2
4CompletedTreatmentMissed Abortion1
4CompletedTreatmentPostpartum Haemorrhage (PPH)1
4CompletedTreatmentPregnancy Termination2
4CompletedTreatmentPregnancy Termination / Pregnancy Trimester, Second1
4CompletedTreatmentPremature Rupture of Membranes at Term2
4CompletedTreatmentSecond Trimester Abortions2
4CompletedTreatmentUnwanted Pregnancies1
4CompletedTreatmentInduction of Uterine contractions1
4Not Yet RecruitingHealth Services ResearchPostpartum Haemorrhage (PPH)1
4Not Yet RecruitingPreventionPost Partum Hemorrhage1
4Not Yet RecruitingPreventionPostpartum Haemorrhage (PPH)1
4Not Yet RecruitingTreatmentAbortion in Second Trimester1
4Not Yet RecruitingTreatmentInduced; Birth / Labor Onset and Length Abnormalities1
4Not Yet RecruitingTreatmentInduction of Labor Affected Fetus / Newborn1
4Not Yet RecruitingTreatmentMedical Abortion1
4Not Yet RecruitingTreatmentMisoprostol, Blood Loss, Myomectomy1
4RecruitingPreventionActive Peptic Ulcer Disease/GI Bleeding1
4RecruitingPreventionCervical Preparation Prior to Hysteroscopy1
4RecruitingPreventionMyomectomy; Surgical Blood Loss1
4RecruitingPreventionPostpartum Haemorrhage (PPH)2
4RecruitingPreventionPregnancy Termination1
4RecruitingPreventionVaginal Misoprostol and Bilateral Uterine Artery Ligation in Decreasing Blood Loss in Trans-abdominal Myomectomy1
4RecruitingTreatmentBMI >30 kg/m2 / Cesarean Delivery / Induction of Uterine contractions1
4RecruitingTreatmentCatheters / Misoprostol / Pregnancy Trimester, Second / Second Trimester Abortions1
4RecruitingTreatmentCervical Ripening / Induction of Labour / Pregnancy1
4RecruitingTreatmentEarly Pregnancy Failure1
4RecruitingTreatmentInduced Deliveries1
4RecruitingTreatmentInduction of Labour1
4RecruitingTreatmentLabor; Forced or Induced, Affecting Fetus or Newborn / Pregnancy1
4RecruitingTreatmentLegally Induced Abortion Without Mention of Complication1
4RecruitingTreatmentLeiomyomas1
4RecruitingTreatmentMiscarriage, Incomplete1
4RecruitingTreatmentMissed Abortion / Pregnancy1
4RecruitingTreatmentSecond Trimester Abortions1
4TerminatedPreventionHemorrhage; Complicating Delivery1
4TerminatedTreatmentPregnancy1
4Unknown StatusTreatmentCervical Ripening1
4Unknown StatusTreatmentInduced / Labour1
4Unknown StatusTreatmentLabour1
4Unknown StatusTreatmentPregnancy Termination / Spontaneous Abortions1
Not AvailableActive Not RecruitingTreatmentSpontaneous Abortions1
Not AvailableCompletedNot AvailableBMI >30 kg/m2 / Induced; Birth1
Not AvailableCompletedNot AvailableComplete Abortion1
Not AvailableCompletedNot AvailableInduction of Labour1
Not AvailableCompletedHealth Services ResearchContraception1
Not AvailableCompletedHealth Services ResearchNeonatal Asphyxia / Postpartum Haemorrhage (PPH)1
Not AvailableCompletedHealth Services ResearchPostpartum Haemorrhage (PPH)1
Not AvailableCompletedHealth Services ResearchPregnancy Termination1
Not AvailableCompletedOtherCervical Ripening1
Not AvailableCompletedPreventionAnemias / Postpartum Haemorrhage (PPH)1
Not AvailableCompletedPreventionPlacenta, Retained / Postpartum Haemorrhage (PPH)1
Not AvailableCompletedPreventionPostpartum Haemorrhage (PPH)3
Not AvailableCompletedPreventionPostpartum Haemorrhage (PPH) / Pregnancy1
Not AvailableCompletedSupportive CareContraception1
Not AvailableCompletedTreatmentCervical Ripening1
Not AvailableCompletedTreatmentContraception2
Not AvailableCompletedTreatmentHysterectomy1
Not AvailableCompletedTreatmentIncomplete Abortion5
Not AvailableCompletedTreatmentInduced; Abortion, Nonmedical1
Not AvailableCompletedTreatmentInduction of Labor in Multiparous Women1
Not AvailableCompletedTreatmentInduction of Labour2
Not AvailableCompletedTreatmentLabor Induction at Term1
Not AvailableCompletedTreatmentLegally Induced Abortion Without Mention of Complication1
Not AvailableCompletedTreatmentOligohydramnios / Pre Eclampsia / Prolonged Pregnancy1
Not AvailableCompletedTreatmentPain1
Not AvailableCompletedTreatmentPain During Hysteroscopy1
Not AvailableCompletedTreatmentPostpartum Haemorrhage (PPH)6
Not AvailableCompletedTreatmentPregnancy1
Not AvailableCompletedTreatmentPregnancy Termination9
Not AvailableCompletedTreatmentSpinal Stenosis of Lumbar Region1
Not AvailableCompletedTreatmentTermination1
Not AvailableCompletedTreatmentTermination of Pregnancy Second Trimester1
Not AvailableEnrolling by InvitationDiagnosticHysteroscopic Surgery / Postoperative pain1
Not AvailableNot Yet RecruitingDiagnosticGYN Disorders1
Not AvailableNot Yet RecruitingDiagnosticPregnancies of Unknown Location (PUL)1
Not AvailableNot Yet RecruitingTreatmentIUD Insertion Complication1
Not AvailableNot Yet RecruitingTreatmentInduction of Abortion1
Not AvailableRecruitingPreventionCesarean Delivery Affecting Fetus / Transient Tachypnea Newborn1
Not AvailableRecruitingPreventionIntrauterine Device1
Not AvailableRecruitingPreventionMaternal Infection During Pregnancy (Diagnosis) / Neonatal Infections1
Not AvailableRecruitingPreventionNeonatal Respiratory Distress1
Not AvailableRecruitingPreventionPregnancy / Premature Rupture of Membranes / Preterm Premature Rupture of Membranes1
Not AvailableRecruitingTreatmentIUD Insertion Complication1
Not AvailableRecruitingTreatmentMissed Abortion1
Not AvailableRecruitingTreatmentPostpartum Haemorrhage (PPH)1
Not AvailableRecruitingTreatmentInduction of Uterine contractions1
Not AvailableSuspendedTreatmentLegally Induced Abortion Without Mention of Complication1
Not AvailableTerminatedTreatmentAbortion, Therapeutic / Pregnancy Trimester, Second1
Not AvailableTerminatedTreatmentAbortions spontaneous / Anembryonic Pregnancy / Early Pregnancy Failure / Fetal Demise1
Not AvailableTerminatedTreatmentContraception1
Not AvailableTerminatedTreatmentGestational Diabetes Mellitus (GDM)1
Not AvailableTerminatedTreatmentPregnancy1
Not AvailableTerminatedTreatmentStenosis of Cervix1
Not AvailableUnknown StatusNot AvailableInduction of Uterine contractions1
Not AvailableUnknown StatusHealth Services ResearchOther Abortion1
Not AvailableUnknown StatusTreatmentAbnormal Uterine Bleeding Unrelated to Menstrual Cycle1
Not AvailableUnknown StatusTreatmentAbortion Techniques / Mifepristone / Misoprostol / Pregnancy Termination1
Not AvailableUnknown StatusTreatmentComplete Abortion1
Not AvailableWithdrawnPreventionPostpartum Haemorrhage (PPH)1

Pharmacoeconomics

Manufacturers
  • Gd searle llc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Packagers
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Cardinal Health
  • Chirogate International Inc.
  • Direct Dispensing Inc.
  • DispenseXpress Inc.
  • Dispensing Solutions
  • GD Searle LLC
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Hawkins Inc.
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
  • Piramal Healthcare
  • Rebel Distributors Corp.
  • Southwood Pharmaceuticals
Dosage forms
FormRouteStrength
Tablet, delayed releaseOral
Tablet, film coatedOral
TabletOral100 ug/1
TabletOral200 ug/1
Kit; tabletBuccal; Oral
TabletOral100 mcg
TabletOral200 mcg
TabletOral
Prices
Unit descriptionCostUnit
Misoprostol hpmc powder152.0USD g
Cytotec 60 200 mcg tablet Bottle121.93USD bottle
Cytotec 60 100 mcg tablet Bottle81.36USD bottle
Arthrotec 75 tablet ec4.07USD tablet
Arthrotec ec 50 mg-200 mcg tablet2.99USD tablet
Arthrotec ec 75 mg-200 mcg tablet2.99USD tablet
Arthrotec ec 75 tablet2.96USD tablet
Arthrotec 75 75-200 mg-mcg tablet2.82USD tablet
Arthrotec 50 50-200 mg-mcg tablet2.7USD tablet
Cytotec 200 mcg tablet1.95USD tablet
Cytotec 100 mcg tablet1.34USD tablet
Misoprostol 200 mcg tablet1.22USD tablet
Misoprostol 100 mcg tablet0.84USD tablet
Apo-Misoprostol 200 mcg Tablet0.45USD tablet
Apo-Misoprostol 100 mcg Tablet0.27USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5601843No1994-02-112014-02-11Us
US5698225No1993-05-032010-05-03Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
water solubility>1.6 mg/mL at 25.0 °CNot Available
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0164 mg/mLALOGPS
logP3.88ALOGPS
logP3.86ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity107.88 m3·mol-1ChemAxon
Polarizability45.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9157
Blood Brain Barrier+0.938
Caco-2 permeable-0.5339
P-glycoprotein substrateSubstrate0.6607
P-glycoprotein inhibitor INon-inhibitor0.7261
P-glycoprotein inhibitor IIInhibitor0.6504
Renal organic cation transporterNon-inhibitor0.9146
CYP450 2C9 substrateNon-substrate0.857
CYP450 2D6 substrateNon-substrate0.9024
CYP450 3A4 substrateSubstrate0.6281
CYP450 1A2 substrateNon-inhibitor0.8358
CYP450 2C9 inhibitorNon-inhibitor0.8175
CYP450 2D6 inhibitorNon-inhibitor0.9459
CYP450 2C19 inhibitorNon-inhibitor0.8199
CYP450 3A4 inhibitorNon-inhibitor0.795
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9591
Ames testNon AMES toxic0.8289
CarcinogenicityNon-carcinogens0.8941
BiodegradationNot ready biodegradable0.8797
Rat acute toxicity3.7051 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.964
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Prostaglandins and related compounds
Alternative Parents
Fatty acid methyl esters / Cyclopentanols / Tertiary alcohols / Methyl esters / Cyclic ketones / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Prostaglandin skeleton / Fatty acid ester / Fatty acid methyl ester / Cyclopentanol / Cyclic alcohol / Tertiary alcohol / Methyl ester / Secondary alcohol / Ketone / Carboxylic acid ester
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Rna polymerase ii transcription factor activity, ligand-activated sequence-specific dna binding
Specific Function
Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition ...
Gene Name
PTGER3
Uniprot ID
P43115
Uniprot Name
Prostaglandin E2 receptor EP3 subtype
Molecular Weight
43309.335 Da
References
  1. Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053]
  2. Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336]
  3. Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143]
  4. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928]
  5. Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the ...
Gene Name
PTGER2
Uniprot ID
P43116
Uniprot Name
Prostaglandin E2 receptor EP2 subtype
Molecular Weight
39759.945 Da
References
  1. Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053]
  2. Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336]
  3. Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143]
  4. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928]
  5. Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. Has a relaxing effect on smooth muscle. May play an important role...
Gene Name
PTGER4
Uniprot ID
P35408
Uniprot Name
Prostaglandin E2 receptor EP4 subtype
Molecular Weight
53118.845 Da
References
  1. Nakae K, Hayashi F, Hayashi M, Yamamoto N, Iino T, Yoshikawa S, Gupta J: Functional role of prostacyclin receptor in rat dorsal root ganglion neurons. Neurosci Lett. 2005 Nov 18;388(3):132-7. [PubMed:16039053]
  2. Li J, Liang X, Wang Q, Breyer RM, McCullough L, Andreasson K: Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett. 2008 Jun 20;438(2):210-5. doi: 10.1016/j.neulet.2008.04.054. Epub 2008 Apr 20. [PubMed:18472336]
  3. Guan Y, Stillman BA, Zhang Y, Schneider A, Saito O, Davis LS, Redha R, Breyer RM, Breyer MD: Cloning and expression of the rabbit prostaglandin EP2 receptor. BMC Pharmacol. 2002 Jun 27;2:14. [PubMed:12097143]
  4. Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [PubMed:9313928]
  5. Nataraj C, Thomas DW, Tilley SL, Nguyen MT, Mannon R, Koller BH, Coffman TM: Receptors for prostaglandin E(2) that regulate cellular immune responses in the mouse. J Clin Invest. 2001 Oct;108(8):1229-35. [PubMed:11602631]
  6. Crider JY, Xu SX, Sharif NA: Pharmacology of functional endogenous IP prostanoid receptors in NCB-20 cells: comparison with binding data from human platelets. Prostaglandins Leukot Essent Fatty Acids. 2001 Nov-Dec;65(5-6):253-8. [PubMed:11993717]

Drug created on June 13, 2005 07:24 / Updated on October 15, 2018 04:36