Synonym
Doripenem Monohydrate; S-4661; DRPM; S 4661; S4661; Finibax; Doribax
IUPAC/Chemical Name
(4S,5R,6R)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5R)-5-((sulfamoylamino)methyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate
InChi Key
NTUBEBXBDGKBTJ-WHLATEEKSA-N
InChi Code
InChI=1S/C15H24N4O6S2.H2O/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25;/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25);1H2/t6-,7+,8+,9-,10-,11-;/m0./s1
SMILES Code
O=C(C(N12)=C(S[C@@H]3CN[C@@H](CNS(=O)(N)=O)C3)[C@@H](C)[C@@]2([H])[C@H]([C@H](O)C)C1=O)O.[H]O[H]
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
Related CAS#
148016-81-3(Doripenem )
364622-82-2(Doripenem Monohydrate)
Biological target:
Doripenem Hydrate (S-4661) is an ultra-broad-spectrum injectable antibiotic, used to treat complicated intra-abdominal infections and complicated urinary tract infections.
In vitro activity:
Doripenem, a new 1-beta-methyl carbapenem, was challenged with a worldwide collection of 394 drug-refractory isolates. For endemic extended-spectrum beta-lactamase- and stably derepressed AmpC-producing enteric bacilli, the doripenem MICs at which 90% of the isolates were inhibited (MIC90s) were 0.03 to 0.5 microg/ml, generally lower than those of comparator carbapenems. A greater proportion of strains among carbapenem-resistant nonfermentative gram-negative bacilli were inhibited by doripenem at < or =4 microg/ml, and doripenem was the most active carbapenem (MIC90, 1 to 4 microg/ml) against penicillin-resistant streptococci.
Reference: Antimicrob Agents Chemother. 2004 Aug;48(8):3136-40. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/15273134/
In vivo activity:
The bacterial counts in lung and liver tissues for all groups are shown in Table 1 and Figure 1. The lung and liver bacterial counts were statistically different between the control and treatment groups for all time points (P<0.05). At 24 h, combination therapies were more effective than doripenem monotherapy. While there were no significant differences between doripenem+sulbactam and oripenem+colistin efficacies, doripenem+amikacin showed better bactericidal activity than these treatments but the tigecycline combination did not. There were no statistical differences in the bacterial loads of lung and liver among combination therapies (P>0.05). However, all combination groups showed a better efficacy than the monotherapy group at 48 h. At 72 h, monotherapy and combination therapies showed the same results on the bacterial counts of lung and liver. Doripenem combinations with tigecycline and with amikacin showed faster bactericidal activity than with colistin and with sulbactam. The doripenem+tigecycline combination was
the most effective therapy decreasing bacterial counts in all groups.
Reference: New Microbiol. 2015 Jan;38(1):67-73. http://www.newmicrobiologica.org/PUB/allegati_pdf/2015/1/67.pdf
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
36.0 |
82.09 |
| Water |
26.0 |
59.29 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
438.51
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.
| 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 |
In vitro protocol:
1. Jones RN, Huynh HK, Biedenbach DJ. Activities of doripenem (S-4661) against drug-resistant clinical pathogens. Antimicrob Agents Chemother. 2004 Aug;48(8):3136-40. doi: 10.1128/AAC.48.8.3136-3140.2004. PMID: 15273134; PMCID: PMC478547.
2. Jones RN, Huynh HK, Biedenbach DJ, Fritsche TR, Sader HS. Doripenem (S-4661), a novel carbapenem: comparative activity against contemporary pathogens including bactericidal action and preliminary in vitro methods evaluations. J Antimicrob Chemother. 2004 Jul;54(1):144-54. doi: 10.1093/jac/dkh298. Epub 2004 Jun 9. PMID: 15190031.
In vivo protocol:
1. Dinc G, Demiraslan H, Elmali F, Ahmed SS, Alp E, Doganay M. Antimicrobial efficacy of doripenem and its combinations with sulbactam, amikacin, colistin, tigecycline in experimental sepsis of carbapenem-resistant Acinetobacter baumannii. New Microbiol. 2015 Jan;38(1):67-73. Epub 2015 Jan 1. PMID: 25742149.
1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Doripenem. 2018 Dec 3. PMID: 29999668.
2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Doripenem. 2017 Jan 17. PMID: 31643441.
3: Anderson DL. Doripenem. Drugs Today (Barc). 2006 Jun;42(6):399-404. doi: 10.1358/dot.2006.42.6.985634. PMID: 16845443.
4: Paterson DL, Depestel DD. Doripenem. Clin Infect Dis. 2009 Jul 15;49(2):291-8. doi: 10.1086/600036. PMID: 19527173.
5: Huang C, Chen I, Yang Y. Doripenem in the Treatment of Patients with Nosocomial Pneumonia: A Meta-Analysis. J Clin Med. 2022 Jul 11;11(14):4014. doi: 10.3390/jcm11144014. PMID: 35887777; PMCID: PMC9319354.
6: Doripenem: S 4661. Drugs R D. 2003;4(6):363-5. doi: 10.2165/00126839-200304060-00006. PMID: 14584966.
7: Wagenlehner FM, Sobel JD, Newell P, Armstrong J, Huang X, Stone GG, Yates K, Gasink LB. Ceftazidime-avibactam Versus Doripenem for the Treatment of Complicated Urinary Tract Infections, Including Acute Pyelonephritis: RECAPTURE, a Phase 3 Randomized Trial Program. Clin Infect Dis. 2016 Sep 15;63(6):754-762. doi: 10.1093/cid/ciw378. Epub 2016 Jun 16. PMID: 27313268; PMCID: PMC4996135.
8: Zhanel GG, Wiebe R, Dilay L, Thomson K, Rubinstein E, Hoban DJ, Noreddin AM, Karlowsky JA. Comparative review of the carbapenems. Drugs. 2007;67(7):1027-52. doi: 10.2165/00003495-200767070-00006. PMID: 17488146.
9: Keam SJ. Doripenem: a review of its use in the treatment of bacterial infections. Drugs. 2008;68(14):2021-57. doi: 10.2165/00003495-200868140-00007. PMID: 18778123.
10: Chahine EB, Ferrill MJ, Poulakos MN. Doripenem: a new carbapenem antibiotic. Am J Health Syst Pharm. 2010 Dec 1;67(23):2015-24. doi: 10.2146/ajhp090672. PMID: 21098373.
11: Shakil S, Danishuddin M, Khan AU. Doripenem versus bacteria: an emerging battleground. J Chemother. 2009 Nov;21(5):482-92. doi: 10.1179/joc.2009.21.5.482. PMID: 19933038.
12: Dedhia HV, McKnight R. Doripenem: position in clinical practice. Expert Rev Anti Infect Ther. 2009 Jun;7(5):507-14. doi: 10.1586/eri.09.37. PMID: 19485791.
13: Matthews SJ, Lancaster JW. Doripenem monohydrate, a broad-spectrum carbapenem antibiotic. Clin Ther. 2009 Jan;31(1):42-63. doi: 10.1016/j.clinthera.2009.01.013. PMID: 19243706.
14: Mandell L. Doripenem: a new carbapenem in the treatment of nosocomial infection. Clin Infect Dis. 2009 Aug 15;49 Suppl 1:S1-3. doi: 10.1086/599809. PMID: 19619016.
15: Guery BP. Le doripénème: quelle place pour un nouveau carbapénème? [Doripenem: need for a new carbapenem]. Med Mal Infect. 2009 Dec;39(12):871-6. French. doi: 10.1016/j.medmal.2009.08.014. Epub 2009 Oct 28. PMID: 19875257.
16: Overturf GD. Doripenem: an early look at a carbapenem not yet approved for pediatrics. Pediatr Infect Dis J. 2010 Feb;29(2):163-5. PMID: 20135831.
17: Papp-Wallace KM, Endimiani A, Taracila MA, Bonomo RA. Carbapenems: past, present, and future. Antimicrob Agents Chemother. 2011 Nov;55(11):4943-60. doi: 10.1128/AAC.00296-11. Epub 2011 Aug 22. PMID: 21859938; PMCID: PMC3195018.
18: Poulakou G, Giamarellou H. Doripenem: an expected arrival in the treatment of infections caused by multidrug-resistant Gram-negative pathogens. Expert Opin Investig Drugs. 2008 May;17(5):749-71. doi: 10.1517/13543784.17.5.749. PMID: 18447600.
19: Zhanel GG, Ketter N, Rubinstein E, Friedland I, Redman R. Overview of seizure-inducing potential of doripenem. Drug Saf. 2009;32(9):709-16. doi: 10.2165/00002018-200932090-00001. PMID: 19670912.
20: Livermore DM. Doripenem: antimicrobial profile and clinical potential. Diagn Microbiol Infect Dis. 2009 Apr;63(4):455-8. doi: 10.1016/j.diagmicrobio.2009.02.012. PMID: 19302929.
