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

MedKoo CAT#: 461364

CAS#: 110221-53-9

Description: Temocaprilat is the diacid of temocapril and an angiotensin-converting enzyme inhibitor.

Chemical Structure

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Temocaprilat
CAS# 110221-53-9
Instruction

Theoretical Analysis

MedKoo Cat#: 461364
Name: Temocaprilat
CAS#: 110221-53-9
Chemical Formula: C21H24N2O5S2
Exact Mass: 448.11
Molecular Weight: 448.550
Elemental Analysis: C, 56.23; H, 5.39; N, 6.25; O, 17.83; S, 14.29

Price and Availability

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5mg USD 770
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Synonym: Temocaprilat; RS-5139; RS 5139; RS5139; RNH 5139; RNH-5139; RNH5139;

IUPAC/Chemical Name: 2-(((2S,6R)-4-(carboxymethyl)-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-6-yl)amino)-4-phenylbutanoic acid

InChi Key: KZVWEOXAPZXAFB-YLGOGADGSA-N

InChi Code: InChI=1S/C21H24N2O5S2/c24-19(25)12-23-11-18(17-7-4-10-29-17)30-13-16(20(23)26)22-15(21(27)28)9-8-14-5-2-1-3-6-14/h1-7,10,15-16,18,22H,8-9,11-13H2,(H,24,25)(H,27,28)/t15?,16-,18-/m0/s1

SMILES Code: O=C(O)CN1C[C@@H](C2=CC=CS2)SC[C@H](NC(C(O)=O)CCC3=CC=CC=C3)C1=O

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: >3 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 448.55 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:
In vitro protocol:
In vivo protocol:

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1: Püchler K, Sierakowski B, Roots I. Single dose and steady state pharmacokinetics of temocapril and temocaprilat in young and elderly hypertensive patients. Br J Clin Pharmacol. 1998 Oct;46(4):363-7. PubMed PMID: 9803985; PubMed Central PMCID: PMC1874161.

2: Yasunari K, Maeda K, Watanabe T, Nakamura M, Asada A, Yoshikawa J. Converting enzyme inhibitor temocaprilat prevents high glucose-mediated suppression of human aortic endothelial cell proliferation. J Cardiovasc Pharmacol. 2003 Dec;42 Suppl 1:S55-60. PubMed PMID: 14871030.

3: Püchler K, Eckl KM, Fritsche L, Renneisen K, Neumayer HH, Sierakowski B, Lavrijssen AT, Thomsen T, Roots I. Pharmacokinetics of temocapril and temocaprilat after 14 once daily oral doses of temocapril in hypertensive patients with varying degrees of renal impairment. Br J Clin Pharmacol. 1997 Dec;44(6):531-6. PubMed PMID: 9431827; PubMed Central PMCID: PMC2042893.

4: Ishizuka H, Konno K, Naganuma H, Nishimura K, Kouzuki H, Suzuki H, Stieger B, Meier PJ, Sugiyama Y. Transport of temocaprilat into rat hepatocytes: role of organic anion transporting polypeptide. J Pharmacol Exp Ther. 1998 Oct;287(1):37-42. PubMed PMID: 9765319.

5: Ishizuka H, Konno K, Naganuma H, Sasahara K, Kawahara Y, Niinuma K, Suzuki H, Sugiyama Y. Temocaprilat, a novel angiotensin-converting enzyme inhibitor, is excreted in bile via an ATP-dependent active transporter (cMOAT) that is deficient in Eisai hyperbilirubinemic mutant rats (EHBR). J Pharmacol Exp Ther. 1997 Mar;280(3):1304-11. PubMed PMID: 9067317.

6: Vistoli G, Pedretti A, Mazzolari A, Bolchi C, Testa B. Influence of ionization state on the activation of temocapril by hCES1: a molecular-dynamics study. Chem Biodivers. 2009 Nov;6(11):2092-100. doi: 10.1002/cbdv.200900174. PubMed PMID: 19937843.

7: Nozawa T, Imai T. Prediction of human intestinal absorption of the prodrug temocapril by in situ single-pass perfusion using rat intestine with modified hydrolase activity. Drug Metab Dispos. 2011 Jul;39(7):1263-9. doi: 10.1124/dmd.110.037937. Epub 2011 Apr 7. PubMed PMID: 21474683.

8: Kamioka M, Ishibashi T, Sugimoto K, Uekita H, Nagai R, Sakamoto N, Ando K, Ohkawara H, Teramoto T, Maruyama Y, Takeishi Y. Blockade of renin-angiotensin system attenuates advanced glycation end products-mediated signaling pathways. J Atheroscler Thromb. 2010 Jun 30;17(6):590-600. Epub 2010 Apr 2. PubMed PMID: 20379053.

9: Takikawa H, Sano N, Onishi T, Toda A, Tanaka H, Hojo M, Marumo T, Hanawa N, Tachizawa H, Nishikawa K. Biliary excretion of taurolithocholate-sulfate and temocaprilat in cholestatic rats induced by bile duct-ligation and ethinylestradiol. Hepatol Res. 2002 Oct;24(2):136. PubMed PMID: 12270742.

10: Hasegawa M, Kusuhara H, Endou H, Sugiyama Y. Contribution of organic anion transporters to the renal uptake of anionic compounds and nucleoside derivatives in rat. J Pharmacol Exp Ther. 2003 Jun;305(3):1087-97. Epub 2003 Mar 26. PubMed PMID: 12660303.

11: Ito N, Ohishi M, Yamamoto K, Tatara Y, Shiota A, Hayashi N, Komai N, Yanagitani Y, Rakugi H, Ogihara T. Renin-angiotensin inhibition reverses advanced cardiac remodeling in aging spontaneously hypertensive rats. Am J Hypertens. 2007 Jul;20(7):792-9. PubMed PMID: 17586415.

12: Shionoiri H, Takasaki I, Minamisawa K, Ishizuka H, Konno K, Naganuma H, Sasahara K, Kawahara Y. Trandolaprilat, an angiotensin-converting enzyme inhibitor, is not excreted in bile via an ATP-dependent active transporter (cMOAT). Hypertens Res. 2001 May;24(3):235-40. PubMed PMID: 11409646.

13: Yamamoto D, Takai S, Akimoto T, Hirahara I, Ito C, Muto S, Kusano E. Matrix metalloproteinase-2 inhibition by temocapril and its important role in peritoneal transport. Clin Exp Pharmacol Physiol. 2012 Oct;39(10):864-8. doi: 10.1111/j.1440-1681.2012.12003.x. PubMed PMID: 23013132.

14: Kawabata H, Ryomoto T, Ishikawa K. Effect of angiotensin converting enzyme inhibitor and angiotensin II type 1 receptor antagonist on metabolism and contraction in ischemia-reperfused rabbit heart. Jpn Circ J. 2000 Apr;64(4):276-82. PubMed PMID: 10783050.

15: Kawabata H, Nakagawa K, Ishikawa K. Effects of an HMG-CoA reductase inhibitor in combination with an ACE inhibitor or angiotensin II type 1 receptor antagonist on myocardial metabolism in ischemic rabbit hearts. Hypertens Res. 2002 Mar;25(2):203-10. PubMed PMID: 12047036.

16: Kawabata H, Ryomoto T, Ishikawa K. Effect of an endothelin receptor antagonist and an angiotensin converting enzyme inhibitor on metabolism and contraction in the ischemic and reperfused rabbit heart. Jpn Circ J. 1999 Oct;63(10):770-4. PubMed PMID: 10553919.

17: Ohura K, Nozawa T, Murakami K, Imai T. Evaluation of transport mechanism of prodrugs and parent drugs formed by intracellular metabolism in Caco-2 cells with modified carboxylesterase activity: temocapril as a model case. J Pharm Sci. 2011 Sep;100(9):3985-94. doi: 10.1002/jps.22628. Epub 2011 May 26. PubMed PMID: 21618543.

18: Arakawa M, Sasaki M, Ohmori M, Harada K, Fujimura A. Pharmacokinetics and pharmacodynamics of temocapril during repeated dosing in elderly hypertensive patients. Eur J Clin Pharmacol. 2001 Jan-Feb;56(11):775-9. PubMed PMID: 11294366.

19: Kitakaze M, Asanuma H, Funaya H, Node K, Takashima S, Sanada S, Asakura M, Ogita H, Kim J, Hori M. Angiotensin-converting enzyme inhibitors and angiotensin II receptor blockers synergistically increase coronary blood flow in canine ischemic myocardium: role of bradykinin. J Am Coll Cardiol. 2002 Jul 3;40(1):162-6. PubMed PMID: 12103271.

20: Kawabata H, Ryomoto T, Ishikawa K. Cardioprotection with angiotensin converting enzyme inhibitor and angiotensin II type 1 receptor antagonist is not abolished by nitric oxide synthase inhibitor in ischemia-reperfused rabbit hearts. Hypertens Res. 2001 Jul;24(4):403-9. PubMed PMID: 11510753.