MedKoo Cat#: 317397 | Name: Cefpiramide Sodium
Featured

Description:

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

Cefpiramide Sodium is a new Pseudomonas-active cephalosporin with a broad spectrum of antibacterial activity. It is the sodium salt form of cefpiramide, a third-generation, semi-synthetic, beta-lactam cephalosporin antibiotic. Cefpiramide Sodium binds to penicillin-binding proteins (PBPs), transpeptidases that are responsible for crosslinking of peptidoglycan.

Chemical Structure

Cefpiramide Sodium
CAS#74849-93-7 (sodium)

Theoretical Analysis

MedKoo Cat#: 317397

Name: Cefpiramide Sodium

CAS#: 74849-93-7 (sodium)

Chemical Formula: C25H23N8NaO7S2

Exact Mass: 0.0000

Molecular Weight: 634.62

Elemental Analysis: C, 47.31; H, 3.65; N, 17.66; Na, 3.62; O, 17.65; S, 10.11

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 1,050.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Synonym
Cefpiramide Sodium; CHEBI:31377; SM-1652; UNII-137KB7GYKB; WY-44635; cefpiramide, sodium salt; SM 1652; SM-1652; Sumcefal;
IUPAC/Chemical Name
sodium;(6R,7R)-7-[[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1H-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
InChi Key
RIWWMGQFMUUYIY-ALLHVENQSA-M
InChi Code
InChI=1S/C25H24N8O7S2.Na/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2;/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40);/q;+1/p-1/t17-,18-,23-;/m1./s1
SMILES Code
CC1=CC(=O)C(=CN1)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@H]3[C@@H]4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)[O-].[Na+]
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, 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 634.62 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
1: Sun Q, Shi M, Shao W, Shi Y, Xi Y, Huang G. Tissue distribution and pulmonary targeting studies of cefpiramide sodium-loaded liposomes. J Drug Target. 2011 Jan;19(1):49-55. doi: 10.3109/10611861003667607. Epub 2010 Mar 5. PubMed PMID: 20205530. 2: Allan JD, Eliopoulos GM, Ferraro MJ, Moellering RC Jr. Comparative in vitro activities of cefpiramide and apalcillin individually and in combination. Antimicrob Agents Chemother. 1985 May;27(5):782-90. PubMed PMID: 3925875; PubMed Central PMCID: PMC180152. 3: Wang H, Yu Y, Xie X, Wang C, Zhang Y, Yuan Y, Zhang X, Liu J, Wang P, Chen M. In-vitro antibacterial activities of cefpiramide and other broad-spectrum antibiotics against 440 clinical isolates in China. J Infect Chemother. 2000 Jun;6(2):81-5. PubMed PMID: 11810540. 4: Guji A, Nishiya H, Aoki M, Ohyatsu I, Yamaguchi M, Tokumura Y, Sugiyama H, Miyashita T, Ono Y, Kunii O. Glutathione S-transferases as a cefpiramide binding protein in rat liver. Pharmacol Toxicol. 1995 Mar;76(3):212-7. PubMed PMID: 7617548. 5: Matsui H, Okuda T. Renal tubular mechanisms for excretion of cefpiramide (SM-1652) in association with its long-lasting pharmacokinetic properties. J Pharmacobiodyn. 1988 Feb;11(2):67-73. PubMed PMID: 3379566. 6: Fu KP, Vince T, McCloud S, Gregory FJ, Chiang ST, Hung PP. Experimental efficacy and pharmacokinetic properties of cefpiramide, a new cephalosporin. Drugs Exp Clin Res. 1985;11(11):787-91. PubMed PMID: 3939215. 7: Nakagawa K, Koyama M, Matsui H, Ikeda C, Yano K, Nakatsuru N, Yoshinaga K, Noguchi T. Pharmacokinetics of cefpiramide (SM-1652) in humans. Antimicrob Agents Chemother. 1984 Feb;25(2):221-5. PubMed PMID: 6712202; PubMed Central PMCID: PMC185478. 8: Takikawa H, Uchida Y, Sano N, Yamanaka M. Biliary cefpiramide excretion: its relation to biliary excretion of bile acids and sulfobromophthalein. Pharmacology. 1995 Jun;51(1):24-32. PubMed PMID: 7568341. 9: Tamai I, Maekawa T, Tsuji A. Membrane potential-dependent and carrier-mediated transport of cefpiramide, a cephalosporin antibiotic, in canalicular rat liver plasma membrane vesicles. J Pharmacol Exp Ther. 1990 May;253(2):537-44. PubMed PMID: 2338647. 10: Brogard JM, Jehl F, Blickle JF, Arnaud JP, Monteil H. Experimental and clinical evaluation of the biliary pharmacokinetic profile of cefpiramide, a new cephalosporin with high hepatic elimination. Drugs Exp Clin Res. 1988;14(8):519-27. PubMed PMID: 3248507. 11: Neu HC, Chin NX. The in vitro activity and beta-lactamase stability of cefpiramide compared with other beta-lactam antibiotics. Diagn Microbiol Infect Dis. 1985 Nov;3(6):479-88. PubMed PMID: 3877607. 12: Barry AL, Jones RN, Thornsberry C, Fuchs PC, Ayers LW, Gavan TL, Gerlach EH, Sommers HM. Cefpiramide: comparative in-vitro activity and beta-lactamase stability. J Antimicrob Chemother. 1985 Sep;16(3):315-25. PubMed PMID: 3877041. 13: Fu KP, Hetzel N, Hung PP, Gregory FJ. Therapeutic efficacy of cefpiramide and cefoperazone alone and in combination with gentamicin against pseudomonal infections in neutropenic mice. Chemotherapy. 1986;32(2):166-72. PubMed PMID: 3698725. 14: Tsuji A, Terasaki T, Takanosu K, Tamai I, Nakashima E. Uptake of benzylpenicillin, cefpiramide and cefazolin by freshly prepared rat hepatocytes. Evidence for a carrier-mediated transport system. Biochem Pharmacol. 1986 Jan 15;35(2):151-8. PubMed PMID: 3080003. 15: Demontes-Mainard F, Vinçon G, Labat L, Amouretti M, Necciari J, Kieffer G, Bannwarth B. Cefpiramide kinetics and plasma protein binding in cholestasis. Br J Clin Pharmacol. 1994 Mar;37(3):295-7. PubMed PMID: 8198940; PubMed Central PMCID: PMC1364762. 16: Brogard JM, Blickle JF, Adloff M, Jehl F, Monteil H. [Cefpiramide, a new cephalosporin with high hepatic elimination; experimental evaluation of its biliary passage and disposition in the liver]. Pathol Biol (Paris). 1989 May;37(5):418-23. French. PubMed PMID: 2780097. 17: Quentin C, Noury P, Titonel M. Comparative in vitro activity of cefpiramide, a new parenteral cephalosporin. Eur J Clin Microbiol Infect Dis. 1988 Aug;7(4):544-9. PubMed PMID: 3141169. 18: Kuleshov SE, Zabrosaev VS, Ovsiankin AV, Petrochenkova NA. [Attempt to use cefpiramide (Tamicin) in patients with infectious destructive lung diseases]. Antibiot Khimioter. 1995 Feb;40(2):51-4. Russian. PubMed PMID: 7605144. 19: Matsui H, Okuda T. Penetration of cefpiramide and cefazolin into peritoneal capsular fluid in rabbits. Antimicrob Agents Chemother. 1988 Jan;32(1):33-6. PubMed PMID: 3348610; PubMed Central PMCID: PMC172093. 20: Fu KP, Hetzel N, Gregory FJ, Hung PP. Therapeutic efficacy of cefpiramide-ciprofloxacin combination in experimental Pseudomonas infections in neutropenic mice. J Antimicrob Chemother. 1987 Oct;20(4):541-6. PubMed PMID: 3680089.