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MedKoo Cat#: 317990 | Name: Hetacillin
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Description:

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

Hetacillin is a beta-lactam antibiotic that is part of the aminopenicillin family. Hetacillin is a prodrug that is converted to ampicillin via esterases. Ampicillin binds to inactivated penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs, including transpeptidases, carboxypeptidases, and endopeptidases, participate in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. It is a prodrug and it has no antibacterial activity itself but quickly splits of acetone in the human body to form ampicillin, which is active against a variety of bacteria.

Chemical Structure

Hetacillin
Hetacillin
CAS#3511-16-8 (free acid)

Theoretical Analysis

MedKoo Cat#: 317990

Name: Hetacillin

CAS#: 3511-16-8 (free acid)

Chemical Formula: C19H23N3O4S

Exact Mass: 389.1409

Molecular Weight: 389.47

Elemental Analysis: C, 58.59; H, 5.95; N, 10.79; O, 16.43; S, 8.23

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
3511-16-8 (free acid) 5321-32-4 (potassium)
Synonym
Hetacillin; Hetacilina; Hetacilline; Hetacillinum; Phenazacillin; Versapen;
IUPAC/Chemical Name
(2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChi Key
DXVUYOAEDJXBPY-NFFDBFGFSA-N
InChi Code
InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2N(C(C)(C)N[C@@H]3C4=CC=CC=C4)C3=O)N1C2=O)O
Appearance
Solid powder
Purity
>95% (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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
A prodrug form of ampicillin.
In vitro activity:
TBD
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 389.47 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:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Kolar QK, Godden SM, Erskine RJ, Ruegg PL. Confirmed bacteriological diagnosis and cure of nonsevere gram-positive clinical mastitis cases enrolled in a randomized clinical trial based on results of on-farm culture. JDS Commun. 2024 May 10;5(6):628-633. doi: 10.3168/jdsc.2024-0560. PMID: 39650047; PMCID: PMC11624340. 2: Vasquez AK, Nydam DV, Capel MB, Ceglowski B, Rauch BJ, Thomas MJ, Tikofsky L, Watters RD, Zuidhof S, Zurakowski MJ. Randomized noninferiority trial comparing 2 commercial intramammary antibiotics for the treatment of nonsevere clinical mastitis in dairy cows. J Dairy Sci. 2016 Oct;99(10):8267-8281. doi: 10.3168/jds.2016-11258. Epub 2016 Aug 10. PMID: 27522408. 3: Lindquist DA, Baynes RE, Smith GW. Short communication: Pharmacokinetics of intramammary hetacillin in dairy cattle milked 3 times per day. J Dairy Sci. 2015 Mar;98(3):1856-61. doi: 10.3168/jds.2014-8715. Epub 2014 Dec 26. PMID: 25547305. 4: Oliveira L, Ruegg PL. Treatments of clinical mastitis occurring in cows on 51 large dairy herds in Wisconsin. J Dairy Sci. 2014 Sep;97(9):5426-36. doi: 10.3168/jds.2013-7756. Epub 2014 Jul 3. PMID: 24997660. 5: Wilson DJ, Gonzalez RN, Case KL, Garrison LL, Gröhn YT. Comparison of seven antibiotic treatments with no treatment for bacteriological efficacy against bovine mastitis pathogens. J Dairy Sci. 1999 Aug;82(8):1664-70. doi: 10.3168/jds.s0022-0302(99)75395-6. PMID: 10480091. 6: Medina MB, Poole DJ, Anderson MR. A screening method for beta-lactams in tissues hydrolyzed with penicillinase I and lactamase II. J AOAC Int. 1998 Sep- Oct;81(5):963-72. PMID: 9772738. 7: Voyksner RD, Tyczkowska KL, Aronson AL. Development of analytical methods for some penicillins in bovine milk by ion-paired chromatography and confirmation by thermospray mass spectrometry. J Chromatogr. 1991 Jul 5;567(2):389-404. doi: 10.1016/0378-4347(91)80145-3. PMID: 1939472. 8: Galanopoulou P, Karageorgiou C, Dimakopoulou K. Effect of enzyme induction on bioavailability of hetacillin in patients treated with anticonvulsants and chlorpromazine. Eur J Drug Metab Pharmacokinet. 1990 Jan-Mar;15(1):15-8. doi: 10.1007/BF03190122. PMID: 2384113. 9: Kitsos M, Massolini G, Gandini C, Caccialanza G. HPLC determination of K-hetacillin and Na-dicloxacillin in oily suspension. Boll Chim Farm. 1989 Jul- Aug;128(7-8):229-31. PMID: 2611008. 10: Mori I, Fujita Y, Ikuta K, Kitano S, Kawabe H, Nakahashi Y, Kato K, Inamori Y. Determination of beta-lactam antibiotics in water by fluorescence quenching of mercurochrome, and application for simple investigation of potency. Chem Pharm Bull (Tokyo). 1989 Jul;37(7):1827-30. doi: 10.1248/cpb.37.1827. PMID: 2478306. 11: Fox LK, Hancock DD, Weems CW, Toma W, Chang E. The effect of intramammary antibiotic therapy at calving on udder health traits. J Dairy Sci. 1987 Aug;70(8):1696-700. doi: 10.3168/jds.S0022-0302(87)80198-4. PMID: 2444634. 12: Gubert S, Palacin C, Sacristán A, Ortiz JA. Synthesis and oral absorption of hetacillin and hetamoxicillin labile esters. Chem Pharm Bull (Tokyo). 1987 Jun;35(6):2366-72. doi: 10.1248/cpb.35.2366. PMID: 3664833. 13: Takahashi M, Ichiman Y, Ohtomo T, Usui Y, Ohshima Y. [Studies on sub-MIC activities of beta-lactam antibiotics and aminoglycoside antibiotics against clinically isolated strain]. Jpn J Antibiot. 1985 Dec;38(12):3497-504. Japanese. PMID: 3938820. 14: Couvaris M, Galanopoulou P, Karageorgiou C, Jalil HA, Varonos D. Bioavailability of hetacillin in rats after liver enzyme induction by various inducers with or without protein binding properties. Eur J Drug Metab Pharmacokinet. 1985 Jan-Mar;10(1):27-32. doi: 10.1007/BF03189694. PMID: 4029217. 15: Tams TR. Management of liver disease in dogs and cats. Mod Vet Pract. 1984 Feb;65(2):107-14. PMID: 6727841. 16: Stavchansky S, Pearlman RS, Van Harken DR, Smyth RD, Hottendorf GH, Martin A, Newburger J, Schneider LW. Evaluation of the bioavailability of sarpicillin, the methoxymethyl ester of hetacillin, in humans. J Pharm Sci. 1984 Feb;73(2):169-73. doi: 10.1002/jps.2600730208. PMID: 6707877. 17: Baker WL. Activity of penicillin-acylase-producing bacteria against alpha- aminobenzylpenicillins. Antonie Van Leeuwenhoek. 1983 Dec;49(6):551-8. doi: 10.1007/BF00399847. PMID: 6424564. 18: Zaremba M, Kacprzak-Wiatr A, Grala-Kałuzna A, Karpińska B, Borowski J, Buśko-Oszczapowicz I, Cieślak J. Penicyliny półsyntetyczne. XXV. Ocena aktywności terapeutycznej chlorowodorku estru acetylometylowego hetacyliny (ceah) na modelach doświadczalnie zakazonych myszy Balb/c pałeczkami gram- ujemnymi [Semisynthetic penicillins. XXV. Therapeutic effect of hetacillin acetylmethyl ester hydrochloride (CEAH) in Balb/c mice experimentally infected with gram-negative bacteria]. Acta Pol Pharm. 1983;40(4):497-506. Polish. PMID: 6673511. 19: Lin JK, Lai CC. Effects of lactobacillus, antacids and antibiotics on the levels of nitrite in the gastro-intestinal tracts of rats fed sodium nitrate. Food Chem Toxicol. 1982 Apr;20(2):197-204. doi: 10.1016/s0278-6915(82)80248-2. PMID: 7044926. 20: Prescription drug products that require patient package inserts; ampicillin and phenytoin--Food and Drug Administration. Final rule. Fed Regist. 1981 Jan 2;46(1):28. PMID: 10249520.

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