L-670596

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 525962

CAS#: 121083-05-4

Description: L-670596 is a potent and selective thromboxane A2/prostaglandin endoperoxide receptor antagonist, also showing ALDH1A1 specific inhibitory activity.


Chemical Structure

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L-670596
CAS# 121083-05-4

Theoretical Analysis

MedKoo Cat#: 525962
Name: L-670596
CAS#: 121083-05-4
Chemical Formula: C22H21F2NO4S
Exact Mass: 433.12
Molecular Weight: 433.470
Elemental Analysis: C, 60.96; H, 4.88; F, 8.77; N, 3.23; O, 14.76; S, 7.40

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: L-670596; L 670596; L670596;

IUPAC/Chemical Name: 2-[6,8-Difluoro-9-[(4-methylsulfonylphenyl)methyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid

InChi Key: GMJWAIMJHBTYPD-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H21F2NO4S/c1-30(28,29)16-7-5-13(6-8-16)12-25-21-14(9-20(26)27)3-2-4-17(21)18-10-15(23)11-19(24)22(18)25/h5-8,10-11,14H,2-4,9,12H2,1H3,(H,26,27)

SMILES Code: O=C(O)CC1C(N(CC2=CC=C(S(=O)(C)=O)C=C2)C3=C4C=C(F)C=C3F)=C4CCC1

Appearance: Solid powder

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

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

More Info:

Product Data:
Biological target: Potent, selective thromboxane A2/prostaglandin endoperoxide antagonist.
In vitro activity: Responses to 8-epi-prostaglandin F2 alpha were unaffected by the selective DP receptor antagonist BW A868C (3-benzyl-5-(6-carboxyhexyl)-1-(2- cyclohexyl-2-hydroxyethylamino)hydantoin) at 50 nM but were blocked by the selective TP receptor antagonist L670596 ((-)6,8-difluoro-9-p-methylsulfonyl benzyl-1,2,3,4- tetrahydrocarbazol-1-yl-acetic acid) at 50 nM. Reference: Eur J Pharmacol. 1995 Oct 16;285(2):151-8. https://pubmed.ncbi.nlm.nih.gov/8566133/
In vivo activity: Newborn rat pups received daily intraperitoneal injections of L670596, a competitive TX A(2) receptor antagonist, or 5,5-dimethyl-3-(3-fluorophenyl)4-(4-methylsulfonyl)phenyl-2(5H)-furanone (DFU), a cyclooxygenase-2 inhibitor, during 14 days of 60% O(2) or air exposure. L670596, but not DFU, prevented 60% O(2)-mediated right ventricular and small pulmonary vessel smooth muscle hypertrophy. Lung ET-1 content was significantly reduced by L670596 in 60% O(2)-exposed animals. Reference: Am J Respir Crit Care Med. 2002 Jul 15;166(2):208-14. https://pubmed.ncbi.nlm.nih.gov/12119234/

Preparing Stock Solutions

The following data is based on the product molecular weight 433.47 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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Crankshaw D. Effects of the isoprostane, 8-epi-prostaglandin F2 alpha, on the contractility of the human myometrium in vitro. Eur J Pharmacol. 1995 Oct 16;285(2):151-8. doi: 10.1016/0014-2999(95)00398-5. PMID: 8566133. 2. Fernandes B, Crankshaw D. Functional characterization of the prostanoid DP receptor in human myometrium. Eur J Pharmacol. 1995 Sep 5;283(1-3):73-81. doi: 10.1016/0014-2999(95)00288-v. PMID: 7498323. 3. Jankov RP, Belcastro R, Ovcina E, Lee J, Massaeli H, Lye SJ, Tanswell AK. Thromboxane A(2) receptors mediate pulmonary hypertension in 60% oxygen-exposed newborn rats by a cyclooxygenase-independent mechanism. Am J Respir Crit Care Med. 2002 Jul 15;166(2):208-14. doi: 10.1164/rccm.200112-124OC. PMID: 12119234. 4. Nuttall GA, Murray MJ, Bowie EJ. Protamine-heparin-induced pulmonary hypertension in pigs: effects of treatment with a thromboxane receptor antagonist on hemodynamics and coagulation. Anesthesiology. 1991 Jan;74(1):138-45. PMID: 1824742.
In vitro protocol: 1. Crankshaw D. Effects of the isoprostane, 8-epi-prostaglandin F2 alpha, on the contractility of the human myometrium in vitro. Eur J Pharmacol. 1995 Oct 16;285(2):151-8. doi: 10.1016/0014-2999(95)00398-5. PMID: 8566133. 2. Fernandes B, Crankshaw D. Functional characterization of the prostanoid DP receptor in human myometrium. Eur J Pharmacol. 1995 Sep 5;283(1-3):73-81. doi: 10.1016/0014-2999(95)00288-v. PMID: 7498323.
In vivo protocol: 1. Jankov RP, Belcastro R, Ovcina E, Lee J, Massaeli H, Lye SJ, Tanswell AK. Thromboxane A(2) receptors mediate pulmonary hypertension in 60% oxygen-exposed newborn rats by a cyclooxygenase-independent mechanism. Am J Respir Crit Care Med. 2002 Jul 15;166(2):208-14. doi: 10.1164/rccm.200112-124OC. PMID: 12119234. 2. Nuttall GA, Murray MJ, Bowie EJ. Protamine-heparin-induced pulmonary hypertension in pigs: effects of treatment with a thromboxane receptor antagonist on hemodynamics and coagulation. Anesthesiology. 1991 Jan;74(1):138-45. PMID: 1824742.

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1: Chakraborty R, Bhullar RP, Dakshinamurti S, Hwa J, Chelikani P. Inverse agonism of SQ 29,548 and Ramatroban on Thromboxane A2 receptor. PLoS One. 2014 Jan 23;9(1):e85937. doi: 10.1371/journal.pone.0085937. eCollection 2014. PubMed PMID: 24465800; PubMed Central PMCID: PMC3900440.

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3: Jankov RP, Belcastro R, Ovcina E, Lee J, Massaeli H, Lye SJ, Tanswell AK. Thromboxane A(2) receptors mediate pulmonary hypertension in 60% oxygen-exposed newborn rats by a cyclooxygenase-independent mechanism. Am J Respir Crit Care Med. 2002 Jul 15;166(2):208-14. PubMed PMID: 12119234.

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7: Crankshaw DJ, Gaspar V. Pharmacological characterization in vitro of prostanoid receptors in the myometrium of nonpregnant ewes. J Reprod Fertil. 1995 Jan;103(1):55-61. PubMed PMID: 7535849.

8: Bannenberg G, Kimland M, Ryrfeldt A, Lundberg JM, Moldéus P. Sensory neuropeptide-mediated bronchoconstriction of the guinea pig lung by diamide; a comparison to hydrogen peroxide. Eur J Pharmacol. 1994 Apr 4;270(2-3):175-82. PubMed PMID: 8039546.

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11: Noguchi K, Noguchi Y, Hirose H, Nishikibe M, Ihara M, Ishikawa K, Yano M. Role of endothelin ETB receptors in bronchoconstrictor and vasoconstrictor responses in guinea-pigs. Eur J Pharmacol. 1993 Mar 16;233(1):47-51. PubMed PMID: 8472748.

12: Vaghi F, Colombo M, Pierucci L, Volpi D, Dho L, Ukmar G, Rosa B, Salvati P. Pharmacological characterization of FCE 27262, a combined thromboxane synthase inhibitor and PGH2/TXA2 receptor antagonist. Drugs Exp Clin Res. 1993;19(6):249-60. PubMed PMID: 8013268.

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17: Nuttall GA, Murray MJ, Bowie EJ. Protamine-heparin-induced pulmonary hypertension in pigs: effects of treatment with a thromboxane receptor antagonist on hemodynamics and coagulation. Anesthesiology. 1991 Jan;74(1):138-45. PubMed PMID: 1824742.

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