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Dinoprostone

Catalog No. DB00917 Name DrugBank
CAS Number 363-24-6 Website http://www.ualberta.ca/
M. F. C20H32O5 Telephone (780) 492-3111
M. W. 352.46508 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 793

SYNONYMS

IUPAC name
(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
IUPAC Traditional name
dinoprostone
Brand Name
Prostarmon E
Prepidil
Prostin E2
Cervidil
Prostin E
Propess
Synonyms
Dinoprostone Prostaglandin E2
PGE2
Prostaglandin E2

DATABASE IDS

CAS Number 363-24-6
PubChem SID 46505549
PubChem CID 5280360

PROPERTIES

Hydrophobicity(logP) 2.8
Solubility 58.1 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description Dinoprostone is a naturally occurring prostaglandin E2 (PGE2). It has important effects in labour. It also stimulates osteoblasts to release factors which stimualtes bone resorption by osteoclasts. As a prescription drug it is used as a vaginal suppository, to prepare the cervix for labour and to induce labour.
Indication For the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. Also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). Other indications include improving the cervical inducibility (cervical "ripening") in pregnant women at or near term with a medical or obstetrical need for labor induction, and the management of postpartum hemorrhage.
Pharmacology Dinoprostone is equivalent to prostaglandin E2 (PGE2). It stimulates labor and delivery by stimulating the uterine, and thus terminates pregnancy. Dinoprostone is also capable of stimulating the smooth muscle of the gastrointestinal tract of man. This activity may be responsible for the vomiting and/or diarrhea that is not uncommon when dinoprostone is used to terminate pregnancy.
Toxicity Oral, mouse: LD50 = 750 mg/kg; Oral, rat: LD50 = 500 mg/kg.
Affected Organisms
Humans and other mammals
Biotransformation Rapid metabolism of dinoprostone occurs primarily in the local tissues; any systemic absorption of the medication is cleared mainly in the maternal lungs and, secondarily, at sites such as the liver and kidneys.
Absorption Absorbed at a rate of 0.3 mg per hour over 12 hours while the vaginal system is in place.
Half Life Less than 5 minutes.
Protein Binding 73%, to albumin
Elimination The major route of elimination of the products of PGE2 metabolism is the kidneys.
External Links
Wikipedia
RxList
Drugs.com

REFERENCES