Synonym
U 12062; U12062; U-12062; Dinoprostone; Prostenone; Prostin; Dinoprostone sodium; PGE2; Prostaglandin E2;
IUPAC/Chemical Name
sodium (Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoate
InChi Key
RNLHOHBNRFOAGH-FNCSRODBSA-M
InChi Code
InChI=1S/C20H32O5.Na/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25;/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);/q;+1/p-1/b7-4-,13-12+;/t15-,16+,17+,19+;/m0./s1
SMILES Code
O=C([O-])CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)CC1=O.[Na+]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
374.45
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Pursley JR, Martins JP, Wright C, Stewart ND. Compared to dinoprost tromethamine, cloprostenol sodium increased rates of estrus detection, conception and pregnancy in lactating dairy cows on a large commercial dairy. Theriogenology. 2012 Sep 1;78(4):823-9. doi: 10.1016/j.theriogenology.2012.03.032. Epub 2012 May 22. PubMed PMID: 22626771.
2: Salverson RR, DeJarnette JM, Marshall CE, Wallace RA. Synchronization of estrus in virgin beef heifers using melengestrol acetate and PGF2alpha: an efficacy comparison of cloprostenol and dinoprost tromethamine. Theriogenology. 2002 Jan 15;57(2):853-8. PubMed PMID: 11991389. 1: Chen W, Xue J, Peprah MK, Wen SW, Walker M, Gao Y, Tang Y. A systematic review and network meta-analysis comparing the use of Foley catheters, misoprostol, and dinoprostone for cervical ripening in the induction of labour. BJOG. 2016 Feb;123(3):346-54. doi: 10.1111/1471-0528.13456. Epub 2015 Nov 5. Review. PubMed PMID: 26538408.
2: Liu A, Lv J, Hu Y, Lang J, Ma L, Chen W. Efficacy and safety of intravaginal misoprostol versus intracervical dinoprostone for labor induction at term: a systematic review and meta-analysis. J Obstet Gynaecol Res. 2014 Apr;40(4):897-906. doi: 10.1111/jog.12333. Review. PubMed PMID: 24698022.
3: Facchinetti F, Fontanesi F, Del Giovane C. Pre-induction of labour: comparing dinoprostone vaginal insert to repeated prostaglandin administration: a systematic review and meta-analysis. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1965-9. doi: 10.3109/14767058.2012.668584. Epub 2012 Apr 2. Review. PubMed PMID: 22372421.
4: Austin SC, Sanchez-Ramos L, Adair CD. Labor induction with intravaginal misoprostol compared with the dinoprostone vaginal insert: a systematic review and metaanalysis. Am J Obstet Gynecol. 2010 Jun;202(6):624.e1-9. doi: 10.1016/j.ajog.2010.03.014. Epub 2010 Apr 28. Review. PubMed PMID: 20430362.
5: Rath W. A clinical evaluation of controlled-release dinoprostone for cervical ripening--a review of current evidence in hospital and outpatient settings. J Perinat Med. 2005;33(6):491-9. Review. PubMed PMID: 16318611.
6: Heckel S, Ohl J, Dellenbach P. [Rupture of an unscarred uterus at full term after an intracervical application of dinoprostone (Prepidil) gel]. Rev Fr Gynecol Obstet. 1993 Mar;88(3):162-4. Review. French. PubMed PMID: 8493447.
7: Santos MD, de la Matta M, Velasco I, Marenco ML. [Disseminated intravascular coagulation associated with the application of dinoprostone gel to the cervix uteri]. Med Clin (Barc). 2000 Oct 21;115(13):518. Review. Spanish. PubMed PMID: 11093878.
3: Nie GJ, Goodin AN, Braden TD, Wenzel JG. Luteal and clinical response following administration of dinoprost tromethamine or cloprostenol at standard intramuscular sites or at the lumbosacral acupuncture point in mares. Am J Vet Res. 2001 Aug;62(8):1285-9. PubMed PMID: 11497452.
4: Bell WR, Wentz AC. Abortion and coagulation by prostaglandin. Intra-amniotic dinoprost tromethamine effect on the coagulation and fibrinolytic systems. JAMA. 1973 Aug 27;225(9):1082-4. PubMed PMID: 4740610.
5: Chebel RC, Santos JE, Rutigliano HM, Cerri RL. Efficacy of an injection of dinoprost tromethamine when given subcutaneously on luteal regression in lactating Holstein cows. Theriogenology. 2007 Feb;67(3):590-7. Epub 2006 Nov 28. PubMed PMID: 17126390.
6: Voh AA Jr, Oyedipe EO, Pathiraja N, Buvanendran V, Kumi-Diaka J. Peripheral plasma levels of progesterone in Nigerian Zebu cows following synchronization of oestrus with prostaglandin F2 alpha analogue (Dinoprost tromethamine). Br Vet J. 1987 May-Jun;143(3):254-63. PubMed PMID: 3594195.
7: Young IM, Anderson DB. Improved reproductive performance from dairy cows treated with dinoprost tromethamine soon after calving. Theriogenology. 1986 Aug;26(2):199-208. PubMed PMID: 16726184.
8: Young IM, Anderson DB. First service conception rate in dairy cows treated with dinoprost tromethamine early post partum. Vet Rec. 1986 Feb 22;118(8):212-3. PubMed PMID: 3716167.
9: Dinoprost tromethamine: first of the new wonder drugs? Nursing. 1974 Oct;4(10):81-2. PubMed PMID: 4497054.
