A stable analog of PGI2
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Carbaprostacyclin

Item No. 18210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6,9α-methylene-11α,15S-dihydroxy-prosta-5E,13E-dien-1-oic acid
CAS Number
69552-46-1
Synonyms
  • Carbacyclin
  • cPGI
Molecular Formula
C21H34O4
Formula Weight
350.5
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >10 mg/ml (from 6B-PGI2)DMSO: >5 mg/ml (from 6B-PGI2)Ethanol: >20 mg/ml (from 6B-PGI2)PBS pH 7.2: >80 µg/ml (from 6B-PGI2)
SMILES
O[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@@H](C/C(C2)=C/CCCC(O)=O)[C@@H]2C1
InChi Code
InChI=1S/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)/b11-10+,15-7+/t16-,17-,18+,19-,20+/m0/s1
InChi Key
XZFRIPGNUQRGPI-WBQKLGIQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

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    Product Description

    Carbaprostacyclin is a stable analog of PGI2. When infused in rabbits or dogs, it inhibits ex vivo platelet aggregation, but the effect persists only 10 minutes after termination of the infusion. This implies rapid metabolic inactivation of carbaprostacyclin.1 Carbaprostacyclin inhibits platelet aggregation with 10% of the molar potency exhibited by PGI2.1,2 The ED50 of carbaprostacyclin for the in vitro inhibition of ADP-induced platelet aggregation in human PRP is 47 nM.3 It was also shown to effect terminal differentiation of preadipose into adipose cells and enhance the expression of angiotensinogen and adipose fatty acid binding protein with an EC50 of about 0.5 µM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Whittle, B.J.R., Moncada, S., Whiting, F., et al. Carbacyclin — a potent stable prostacyclin analogue for the inhibition of platelet aggregation. Prostaglandins 19(4), 605-627 (1980).

    2. Aiken, J.W., and Shebuski, R.J. Comparison in anesthetized dogs of the anti-aggregatory and hemodynamic effects of prostacyclin and a chemically stable prostacyclin analog, 6a-carba-PGI2 (carbacyclin). Prostaglandins 19(4), 629-643 (1980).

    3. Adaikan, P.G., Karim, S.M.M., and Lau, L.C. Platelet and other effects of carbaprostacyclin - a stable prostacyclin analogue. Prostaglandins Med. 5(4), 307-320 (1980).

    4. Aubert, J., Ailhaud, G., and Negrel, R. Evidence for a novel regulatory pathway activated by (carba)prostacyclin in preadipose and adipose cells. FEBS Lett. 397(1), 117-121 (1996).

    Product Citations

    Woodward, D.F., Krauss, A.H.P., Chen, J., et al. Pharmacological characterization of a novel antiglaucoma agent, bimatoprost (AGN 192024). J. Pharmacol. Exp. Ther. 305(2), 772-785 (2003).