ID

DB08964||

名称

Gemeprost

描述

Gemeprost is a prostaglandin E1 (PGE1) analog and antiprogestogen used for preoperative dilation of the cervix before surgical abortion. It is available as vaginal suppositories and also used in combination with the antiprogestin and mifepristone for termination of 1st- and 2nd-trimester pregnancy [A19726]. It is not FDA-approved but available in Japan marketed as Preglandin.

cas号

64318-79-2

唯一标识码

45KZB1FOLS

状态

liquid

组

approved,withdrawn,

指示

Indicated for the softening and dilatation of the cervix uteri prior to transcervical, intrauterine operative procedures in the first trimester of pregnancy or facilitating therapeutic termination of pregnancy in patients in the second trimester of gestation.

药效学

Gemeprost softens and dilates of the cervix prior to transcervical intrauterine operative procedures. It is a prostaglandin E1 analog that potently stimulates uterine contractions and causes cervical ripening and relaxation [A19726].

作用机制

As a prostaglandin analog, gemeprost binds to prostaglandin E2 and E3 receptors as an agonist to cause myometrial contractions and progressive cervical dilation via tissue sensitization to oxytocin [A19732].

毒性

Serious or life-threatening adverse effects include coronary spasms with subsequent myocardial infarctions and uterine rupture following prolonged uterine hypertonia or abnormal uterine pain. More common adverse effects are nausea, vomiting, loose stools, diarrhea, lower abdominal or back pain, headache, mild pyrexia and flushing. Less common side effects include hypotension, chest pain palpitations, tachycardia, muscle weakness, dyspnea, chills and headache. Oral LD50 is 300 mg/kg in mouse, 980 mg/kg in rat and 3200 mg/kg in rabbit [MSDS].

代谢

After intravenous administration, gemeprost is rapidly metabolized via hydrolysis to the free acid with half life of 10-15 minutes. The free acid is then inactivated by β- and ω-oxidation [A19726].

吸收

Systemic absorption of gemeprost is limited with about 12-28% of administered dose of gemeprost reaching the systemic circulation [L878]. Following vaginal administration, peak plasma concentration is reached after 2-3 hours [A19726].

半衰期

分类

description:This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
direct-parent:Fatty alcohols
kingdom:Organic compounds
superclass:Lipids and lipid-like molecules
class:Fatty Acyls
subclass:Fatty alcohols
alternative-parent:Cyclic alcohols and derivatives
alternative-parent:Cyclic ketones
alternative-parent:Cyclopentanols
alternative-parent:Enoate esters
alternative-parent:Fatty acid esters
alternative-parent:Hydrocarbon derivatives
alternative-parent:Methyl esters
alternative-parent:Monocarboxylic acids and derivatives
alternative-parent:Organic oxides
substituent:Alcohol
substituent:Aliphatic homomonocyclic compound
substituent:Alpha,beta-unsaturated carboxylic ester
substituent:Carbonyl group
substituent:Carboxylic acid derivative
substituent:Carboxylic acid ester
substituent:Cyclic alcohol
substituent:Cyclic ketone
substituent:Cyclopentanol
substituent:Enoate ester
substituent:Fatty acid ester
substituent:Fatty alcohol
substituent:Hydrocarbon derivative
substituent:Ketone
substituent:Methyl ester
substituent:Monocarboxylic acid or derivatives
substituent:Organic oxide
substituent:Organic oxygen compound
substituent:Organooxygen compound
substituent:Secondary alcohol

消除途径

About 50% of the dose eliminated as metabolites in the urine during the first 24 hours.

种类

Abortifacient Agents
D000019
Abortifacient Agents, Nonsteroidal
D000020
Autacoids
D012898
Biological Factors
D001685
Drugs that are Mainly Renally Excreted

Eicosanoids
D015777
Fatty Acids
D005227
Fatty Acids, Monounsaturated
D005229
Fatty Acids, Unsaturated
D005231
Genito Urinary System and Sex Hormones

Inflammation Mediators
D018836
Lipids
D008055
Prostaglandins
D011453
Prostaglandins E
D011458
Prostaglandins E, Synthetic
D011459
Reproductive Control Agents
D012102
Uterotonic agents
D010120

盐类

蛋白质结合

清除

同义词

language:english; code:; name;16,16-Dimethyl-trans-delta-2-PGE1 methyl ester
language:english; code:; name;16,16-Dimethyl-trans-delta(sup 2)-prostaglandin E1 methyl ester
language:english; code:; name;SC-37681

国际品牌

CergemMSD Merck Sharp & DohmeCervagemSanofiCervagèmeSanofi-AventisCervidilMerck Serono

配送量

产品

混合物

包装者

生产者

价格

受影响的生物体

剂量

form:Suppository
route:Vaginal
strength:1 MG

atc代码

Prostaglandins
UTEROTONICS
OTHER GYNECOLOGICALS
GENITO URINARY SYSTEM AND SEX HORMONES

fda标签

化学品安全技术说明书

//s3-us-west-2.amazonaws.com/drugbank/msds/DB08964.pdf?1498843666

专利

食物相互作用

药物相互作用

序列

实验性质

外部标识符

resource：ChEBI
identifier：135626
resource：PubChem Compound
identifier：5282237
resource：PubChem Substance
identifier：310264927
resource：KEGG Drug
identifier：D02073
resource：ChemSpider
identifier：4445416
resource：Wikipedia
identifier：Gemeprost
resource：ChEMBL
identifier：CHEMBL1908315
resource：ZINC
identifier：ZINC000004216393
resource：RxCUI
identifier：12449

外部链接

路径

目标

id:BE0000368
name:Prostaglandin E2 receptor EP2 subtype
organism:Humans
action:agonist
Matsuya H, Sekido N, Kida J, Mashimo H, Wakamatsu D, Okada H: Effects of an EP2 and EP3 Receptor Dual Agonist, ONO-8055, on a Radical Hysterectomy-Induced Underactive Bladder Model in Monkeys. Low Urin Tract Symptoms. 2017 Apr 25. doi: 10.1111/luts.12166.
known-action:unknown
name:Prostaglandin E2 receptor EP2 subtype
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 relaxing effect of this receptor on smooth muscle.
gene-name:PTGER2
locus:14q22
cellular-location:Cell membrane
transmembrane-regions:24-47 66-91 112-132 152-176 199-223 263-286 300-323
signal-regions:
theoretical-pi:9.19
molecular-weight:39759.945
chromosome-location:14
organism:Humans
external-identifiers:HUGO Gene Nomenclature Committee (HGNC)HGNC:9594GenAtlasPTGER2GenBank Gene DatabaseU19487GenBank Protein Database632650IUPHAR341Guide to Pharmacology341UniProtKBP43116UniProt AccessionPE2R2_HUMAN
synonyms:PGE receptor EP2 subtypeProstanoid EP2 receptor
amino-acid-sequence:>lcl|BSEQ0010263|Prostaglandin E2 receptor EP2 subtype MGNASNDSQSEDCETRQWLPPGESPAISSVMFSAGVLGNLIALALLARRWRGDVGCSAGR RSSLSLFHVLVTELVFTDLLGTCLISPVVLASYARNQTLVALAPESRACTYFAFAMTFFS LATMLMLFAMALERYLSIGHPYFYQRRVSRSGGLAVLPVIYAVSLLFCSLPLLDYGQYVQ YCPGTWCFIRHGRTAYLQLYATLLLLLIVSVLACNFSVILNLIRMHRRSRRSRCGPSLGS GRGGPGARRRGERVSMAEETDHLILLAIMTITFAVCSLPFTIFAYMNETSSRKEKWDLQA LRFLSINSIIDPWVFAILRPPVLRLMRSVLCCRISLRTQDATQTSCSTQSDASKQADL
gene-sequence:>lcl|BSEQ0010264|Prostaglandin E2 receptor EP2 subtype (PTGER2) ATGGGCAATGCCTCCAATGACTCCCAGTCTGAGGACTGCGAGACGCGACAGTGGCTTCCC CCAGGCGAAAGCCCAGCCATCAGCTCCGTCATGTTCTCGGCCGGGGTGCTGGGGAACCTC ATAGCACTGGCGCTGCTGGCGCGCCGCTGGCGGGGGGACGTGGGGTGCAGCGCCGGCCGC AGGAGCTCCCTCTCCTTGTTCCACGTGCTGGTGACCGAGCTGGTGTTCACCGACCTGCTC GGGACCTGCCTCATCAGCCCAGTGGTACTGGCTTCGTACGCGCGGAACCAGACCCTGGTG GCACTGGCGCCCGAGAGCCGCGCGTGCACCTACTTCGCTTTCGCCATGACCTTCTTCAGC CTGGCCACGATGCTCATGCTCTTCGCCATGGCCCTGGAGCGCTACCTCTCGATCGGGCAC CCCTACTTCTACCAGCGCCGCGTCTCGCGCTCCGGGGGCCTGGCCGTGCTGCCTGTCATC TATGCAGTCTCCCTGCTCTTCTGCTCGCTGCCGCTGCTGGACTATGGGCAGTACGTCCAG TACTGCCCCGGGACCTGGTGCTTCATCCGGCACGGGCGGACCGCTTACCTGCAGCTGTAC GCCACCCTGCTGCTGCTTCTCATTGTCTCGGTGCTCGCCTGCAACTTCAGTGTCATTCTC AACCTCATCCGCATGCACCGCCGAAGCCGGAGAAGCCGCTGCGGACCTTCCCTGGGCAGT GGCCGGGGCGGCCCCGGGGCCCGCAGGAGAGGGGAAAGGGTGTCCATGGCGGAGGAGACG GACCACCTCATTCTCCTGGCTATCATGACCATCACCTTCGCCGTCTGCTCCTTGCCTTTC ACGATTTTTGCATATATGAATGAAACCTCTTCCCGAAAGGAAAAATGGGACCTCCAAGCT CTTAGGTTTTTATCAATTAATTCAATAATTGACCCTTGGGTCTTTGCCATCCTTAGGCCT CCTGTTCTGAGACTAATGCGTTCAGTCCTCTGTTGTCGGATTTCATTAAGAACACAAGAT GCAACACAAACTTCCTGTTCTACACAGTCAGATGCCAGTAAACAGGCTGACCTTTGA
pfams:PF000017tm_1
go-classifiers:componentintegral component of plasma membranecomponentplasma membranefunctionprostaglandin E receptor activityprocessadenylate cyclase-activating G-protein coupled receptor signaling pathwayprocesscellular response to prostaglandin E stimulusprocessG-protein coupled receptor signaling pathwayprocessregulation of cell proliferationprocessresponse to lipopolysaccharideprocessresponse to progesterone
id:BE0002375
name:Prostaglandin E2 receptor EP3 subtype
organism:Humans
action:agonist
Qian YM, Jones RL, Chan KM, Stock AI, Ho JK: Potent contractile actions of prostanoid EP3-receptor agonists on human isolated pulmonary artery. Br J Pharmacol. 1994 Oct;113(2):369-74.
Matsuya H, Sekido N, Kida J, Mashimo H, Wakamatsu D, Okada H: Effects of an EP2 and EP3 Receptor Dual Agonist, ONO-8055, on a Radical Hysterectomy-Induced Underactive Bladder Model in Monkeys. Low Urin Tract Symptoms. 2017 Apr 25. doi: 10.1111/luts.12166.
known-action:yes
name:Prostaglandin E2 receptor EP3 subtype
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 of sodium and water reabsorption in kidney tubulus and contraction in uterine smooth muscle. The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G-I proteins, and to an elevation of intracellular calcium. The various isoforms have identical ligand binding properties but can interact with different second messenger systems (By similarity).
gene-name:PTGER3
locus:1p31.2
cellular-location:Cell membrane
transmembrane-regions:54-78 92-112 132-153 176-197 228-253 284-307 328-349
signal-regions:
theoretical-pi:10.05
molecular-weight:43309.335
chromosome-location:1
organism:Humans
external-identifiers:HUGO Gene Nomenclature Committee (HGNC)HGNC:9595GenAtlasPTGER3GenBank Gene DatabaseS69200IUPHAR342Guide to Pharmacology342UniProtKBP43115UniProt AccessionPE2R3_HUMAN
synonyms:PGE receptor EP3 subtypePGE2-RProstanoid EP3 receptor
amino-acid-sequence:>lcl|BSEQ0004665|Prostaglandin E2 receptor EP3 subtype MKETRGYGGDAPFCTRLNHSYTGMWAPERSAEARGNLTRPPGSGEDCGSVSVAFPITMLL TGFVGNALAMLLVSRSYRRRESKRKKSFLLCIGWLALTDLVGQLLTTPVVIVVYLSKQRW EHIDPSGRLCTFFGLTMTVFGLSSLFIASAMAVERALAIRAPHWYASHMKTRATRAVLLG VWLAVLAFALLPVLGVGQYTVQWPGTWCFISTGRGGNGTSSSHNWGNLFFASAFAFLGLL ALTVTFSCNLATIKALVSRCRAKATASQSSAQWGRITTETAIQLMGIMCVLSVCWSPLLI MMLKMIFNQTSVEHCKTHTEKQKECNFFLIAVRLASLNQILDPWVYLLLRKILLRKFCQI RYHTNNYASSSTSLPCQCSSTLMWSDHLER
gene-sequence:>lcl|BSEQ0011703|Prostaglandin E2 receptor EP3 subtype (PTGER3) ATGAAGGAGACCCGGGGCTACGGAGGGGATGCCCCCTTCTGCACCCGCCTCAACCACTCC TACACAGGCATGTGGGCGCCCGAGCGTTCCGCCGAGGCGCGGGGCAACCTCACGCGCCCT CCAGGGTCTGGCGAGGATTGCGGATCGGTGTCCGTGGCCTTCCCGATCACCATGCTGCTC ACTGGTTTCGTGGGCAACGCACTGGCCATGCTGCTCGTGTCGCGCAGCTACCGGCGCCGG GAGAGCAAGCGCAAGAAGTCCTTCCTGCTGTGCATCGGCTGGCTGGCGCTCACCGACCTG GTCGGGCAGCTTCTCACCACCCCGGTCGTCATCGTCGTGTACCTGTCCAAGCAGCGTTGG GAGCACATCGACCCGTCGGGGCGGCTCTGCACCTTTTTCGGGCTGACCATGACTGTTTTC GGGCTCTCCTCGTTGTTCATCGCCAGCGCCATGGCCGTCGAGCGGGCGCTGGCCATCAGG GCGCCGCACTGGTATGCGAGCCACATGAAGACGCGTGCCACCCGCGCTGTGCTGCTCGGC GTGTGGCTGGCCGTGCTCGCCTTCGCCCTGCTGCCGGTGCTGGGCGTGGGCCAGTACACC GTCCAGTGGCCCGGGACGTGGTGCTTCATCAGCACCGGGCGAGGGGGCAACGGGACTAGC TCTTCGCATAACTGGGGCAACCTTTTCTTCGCCTCTGCCTTTGCCTTCCTGGGGCTCTTG GCGCTGACAGTCACCTTTTCCTGCAACCTGGCCACCATTAAGGCCCTGGTGTCCCGCTGC CGGGCCAAGGCCACGGCATCTCAGTCCAGTGCCCAGTGGGGCCGCATCACGACCGAGACG GCCATTCAGCTTATGGGGATCATGTGCGTGCTGTCGGTCTGCTGGTCTCCGCTCCTGATA ATGATGTTGAAAATGATCTTCAATCAGACATCAGTTGAGCACTGCAAGACACACACGGAG AAGCAGAAAGAATGCAACTTCTTCTTAATAGCTGTTCGCCTGGCTTCACTGAACCAGATC TTGGATCCTTGGGTTTACCTGCTGTTAAGAAAGATCCTTCTTCGAAAGTTTTGCCAGATC AGGTACCACACAAACAACTATGCATCCAGCTCCACCTCCTTACCCTGCCAGTGTTCCTCA ACCTTGATGTGGAGCGACCATTTGGAAAGATGA
pfams:PF000017tm_1
go-classifiers:componentcytosolcomponentintegral component of membranecomponentintegral component of plasma membranecomponentnuclear envelopecomponentplasma membranefunctionprostaglandin E receptor activityfunctionRNA polymerase II transcription factor activity, ligand-activated sequence-specific DNA bindingprocessadenylate cyclase-modulating G-protein coupled receptor signaling pathwayprocessbicarbonate transportprocesscell deathprocessfever generationprocessG-protein coupled receptor signaling pathwayprocessintracellular receptor signaling pathwayprocessphospholipase C-activating G-protein coupled receptor signaling pathwayprocesspositive regulation of cytosolic calcium ion concentrationprocesspositive regulation of fever generationprocesspositive regulation of urine volumeprocessresponse to lipopolysaccharideprocesstranscription, DNA-templated

酶

载体

运输工具

药物反应

效应

不良反应