A stable, isosteric PGD2 analog
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11-deoxy-11-methylene Prostaglandin D2

Item No. 12410

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,15S-dihydroxy-11-methylene-prosta-5Z,13E-dien-1-oic acid
CAS Number
100648-29-1
Synonyms
  • 11-deoxy-11-methylene PGD2
Molecular Formula
C21H34O4
Formula Weight
350.5
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 100 mg/mlEthanol: 100 mg/mlPBS (pH 7.2): 3.75 mg/ml
SMILES
O[C@@H](C1)[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)C1=C
InChi Code
InChI=1S/C21H34O4/c1-3-4-7-10-17(22)13-14-18-16(2)15-20(23)19(18)11-8-5-6-9-12-21(24)25/h5,8,13-14,17-20,22-23H,2-4,6-7,9-12,15H2,1H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19+,20-/m0/s1
InChi Key
ROZAFJXVUNORLT-SFIVEXQWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $79

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    5 mg

    $345

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    10 mg

    $610

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    Product Description

    Prostaglandin D2 (PGD2; Item No. 12010) is one of the five primary enzymatic prostaglandins derived directly from PGH2 (Item No. 17020). PGD2 is produced abundantly in the CSF by the lipocalin-type PGD synthase, and in the periphery by myeloid cells including mast cells and basophils by a second, leukocyte-type PGD synthase.1 PGD2 is chemically unstable, and its use and analysis is complicated by its short in vivo half-life. 11-deoxy-11-methylene PGD2 is a novel, chemically stable, isosteric analog of PGD2 wherein the 11-keto group is replaced by an exocyclic methylene. In the PGE series, the analogous modification leads to a stable, somewhat less potent agonist which embodies the same uterine stimulant and cervical ripening activities as the parent prostaglandin.2 However, 11-deoxy-11-methylene PGD2 has been reported by one group to be essentially without agonist activity on human platelets, a DP1 receptor assay.3 The CRTH2-receptor actions of 11-deoxy-11-methylene PGD2 are not yet reported.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Urade, Y., and Hayaishi, O. Prostaglandin D synthase: Structure and function. Vitam. Horm. 58, 89-120 (2000).

    2. Borten, M., DiLeo, L.A., and Friedman, E.A. Low-dose prostaglandin E2 analogue for cervical dilations prior to pregnancy termination. Am. J. Obstet. Gynecol. 150(5 Pt 1), 561-565 (1984).

    3. Torisawa, Y., Yamaguchi, T., Sakata, S., et al. Synthesis of 11-deoxo-11-methylene-prostaglandin D2 and its derivatives. Chem. Pharm. Bull. (Tokyo) 33(10), 4625-4628 (1985).