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MedKoo Cat#: 464415 | Name: Ornidazole-d5
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Description:

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

Ornidazole-d5 is intended for use as an internal standard for the quantification of ornidazole by GC- or LC-MS. Ornidazole is an orally bioavailable 5-nitroimidazole derivative with antibacterial and antiprotozoal activities. Ornidazole inhibits the growth of clinical isolates of B. fragilis (MICs = 0.5-5 μM) and various anaerobic bacteria when used at concentrations ranging from less than 0.1 to 3.2 μg/ml. It also inhibits the growth of Giardia isolates (IC50s = 0.01-0.47 μg/ml). Oral administration of ornidazole reduces T. vaginalis and T. foetus infection in mice and E. histolytica infection in rats with curative dose (CD50) values of 37, 3, and 10 mg/kg, respectively. Ornidazole (400 mg/kg per day) induces infertility in male rats within 7 days and inhibits spermatozoa binding to rat oocyte zona pellucida.

Chemical Structure

Ornidazole-d5
Ornidazole-d5
CAS#2747915-64-4

Theoretical Analysis

MedKoo Cat#: 464415

Name: Ornidazole-d5

CAS#: 2747915-64-4

Chemical Formula: C7H5D5ClN3O3

Exact Mass: 224.0725

Molecular Weight: 224.66

Elemental Analysis: C, 37.42; H, 6.73; Cl, 15.78; N, 18.70; O, 21.36

Price and Availability

Size Price Availability Quantity
1mg USD 380.00 2 Weeks
5mg USD 1,240.00 2 Weeks
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Synonym
Ornidazole-d5; Ornidazole d5; (±)-Ornidazole-d5; (±) Ornidazole-d5;
IUPAC/Chemical Name
1-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-1,1,2,3,3-d5-2-ol
InChi Key
IPWKIXLWTCNBKN-VLZDWVQFSA-N
InChi Code
InChI=1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3/i2D2,4D2,6D
SMILES Code
OC([2H])(C([2H])(N1C(C)=NC=C1[N+]([O-])=O)[2H])C([2H])(Cl)[2H]
Appearance
Solid powder
Purity
>99% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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:
Ornidazole-d5 is intended for use as an internal standard for the quantification of ornidazole by GC- or LC-MS. Ornidazole is an orally bioavailable 5-nitroimidazole derivative with antibacterial and antiprotozoal activities.
In vitro activity:
In an attempt to understand, if ornidazole, a known anti-fertility drug, adversely affects sperm functions by targeting capacitation, this study designed experiments to study the influence of this drug on hyperactivation (HA), capacitation-associated protein tyrosine phosphorylation (pY) and the acrosome reaction (AR). Addition of ornidazole at 0 h, inhibited the onset of HA and total pY in a dose dependent manner. Reference: Reprod Toxicol. 2006 Nov;22(4):702-9. https://pubmed.ncbi.nlm.nih.gov/16777375/
In vivo activity:
Rats were provided with free access to water containing ornidazole (1 g/L) or drinking water only for 14 days. Once the rats were euthanized (ornidazole group, n = 16; control group, n = 14), histological signatures and the volumes of endometriosis lesions were assessed. The median lesion volume was lower in the ornidazole group (20.2 mm3; range, 5.7-53.3 mm3) than in the control group (81.3 mm3; range, 32.8-122.2 mm3; p = 0.007). Median IL-1β cell counts were 5.3 (range, 4.5-6.4) for ornidazole and 11.7 (range, 9.4-15.4) for control (p < 0.001). Mean IL-6 cell counts were 5.6 ± 1.8 for ornidazole and 11.3 ± 4.1 for control (p < 0.001). Median TNF-α cell counts were 5.7 (range, 4.5-7.2) for ornidazole and 12.1 (range, 10.0-15.9) for control (p < 0.001). Median VEGF cell counts were 8.1 (range, 6.5-11.4) for ornidazole and 18.3 (range, 14.2-21.0) for control (p = 0.001). Reference: Gynecol Obstet Invest. 2022;87(5):316-323. https://pubmed.ncbi.nlm.nih.gov/36265450/

Preparing Stock Solutions

The following data is based on the product molecular weight 224.66 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. Marcus Y, Tal N, Ronen M, Carmieli R, Gurevitz M. The drug ornidazole inhibits photosynthesis in a different mechanism described for protozoa and anaerobic bacteria. Biochem J. 2016 Dec 1;473(23):4413-4426. doi: 10.1042/BCJ20160433. Epub 2016 Sep 19. Erratum in: Biochem J. 2017 Dec 14;474(24):4269. PMID: 27647935. 2. Siva AB, Yeung CH, Cooper TG, Shivaji S. Antimicrobial drug ornidazole inhibits hamster sperm capacitation, in vitro. Reprod Toxicol. 2006 Nov;22(4):702-9. doi: 10.1016/j.reprotox.2006.04.013. Epub 2006 Jun 14. PMID: 16777375. 3. Evyapan G, Luleyap U, Kaplan HM, Kara IO. Ornidazole suppresses CD133+ melanoma stem cells via inhibiting hedgehog signaling pathway and inducing multiple death pathways in a mouse model. Croat Med J. 2022 Oct 31;63(5):461-474. doi: 10.3325/cmj.2022.63.461. PMID: 36325671; PMCID: PMC9648086. 4. Qin X, Yang H, Qiao D, Liu X, Liu LB, Liu SF, Jia Z. Ornidazole Reduces the Progression of Endometriosis in a Rat Model. Gynecol Obstet Invest. 2022;87(5):316-323. doi: 10.1159/000527515. Epub 2022 Oct 20. PMID: 36265450; PMCID: PMC9808641.
In vitro protocol:
1. Marcus Y, Tal N, Ronen M, Carmieli R, Gurevitz M. The drug ornidazole inhibits photosynthesis in a different mechanism described for protozoa and anaerobic bacteria. Biochem J. 2016 Dec 1;473(23):4413-4426. doi: 10.1042/BCJ20160433. Epub 2016 Sep 19. Erratum in: Biochem J. 2017 Dec 14;474(24):4269. PMID: 27647935. 2. Siva AB, Yeung CH, Cooper TG, Shivaji S. Antimicrobial drug ornidazole inhibits hamster sperm capacitation, in vitro. Reprod Toxicol. 2006 Nov;22(4):702-9. doi: 10.1016/j.reprotox.2006.04.013. Epub 2006 Jun 14. PMID: 16777375.
In vivo protocol:
1. Evyapan G, Luleyap U, Kaplan HM, Kara IO. Ornidazole suppresses CD133+ melanoma stem cells via inhibiting hedgehog signaling pathway and inducing multiple death pathways in a mouse model. Croat Med J. 2022 Oct 31;63(5):461-474. doi: 10.3325/cmj.2022.63.461. PMID: 36325671; PMCID: PMC9648086. 2. Qin X, Yang H, Qiao D, Liu X, Liu LB, Liu SF, Jia Z. Ornidazole Reduces the Progression of Endometriosis in a Rat Model. Gynecol Obstet Invest. 2022;87(5):316-323. doi: 10.1159/000527515. Epub 2022 Oct 20. PMID: 36265450; PMCID: PMC9808641.
1: Teoh L, Cheung MC, Dashper S, James R, McCullough MJ. Oral Antibiotic for Empirical Management of Acute Dentoalveolar Infections-A Systematic Review. Antibiotics (Basel). 2021 Feb 28;10(3):240. doi: 10.3390/antibiotics10030240. PMID: 33670844; PMCID: PMC7997333. 2: Iali W, Moustafa GAI, Dagys L, Roy SS. 15 N hyperpolarisation of the antiprotozoal drug ornidazole by Signal Amplification By Reversible Exchange in aqueous medium. Magn Reson Chem. 2021 Mar 3. doi: 10.1002/mrc.5144. Epub ahead of print. PMID: 33656772. 3: Harika S, Kumar YS, Rao YM, Sriram P, Shankar U. Design and Evaluation of Ornidazole Sustained release Dental Inserts. Curr Drug Metab. 2021 Feb 22. doi: 10.2174/1389200222666210222152940. Epub ahead of print. PMID: 33618642. 4: Siwach A, Verma PK. Synthesis and therapeutic potential of imidazole containing compounds. BMC Chem. 2021 Feb 18;15(1):12. doi: 10.1186/s13065-020-00730-1. PMID: 33602331; PMCID: PMC7893931. 5: Fedorych P. DIAGNOSTICS AND TREATMENT OF GENITAL INVASION CAUSED BY TRICHOMONAS VAGINALIS AND POSSIBLY OTHER RELATED SPECIES (PENTATRICHOMONAS HOMINIS AND TRICHOMONAS TENAX) IN PATIENTS WITH IMMUNODEFICIENCY. Georgian Med News. 2020 Dec;(309):81-85. PMID: 33526734. 6: Venkatesh K, Rajakumaran R, Chen SM, Karuppiah C, Yang CC, Ramaraj SK, Ali MA, Al-Hemaid FMA, El-Shikh MS, Almunqedhi BMA. A novel hybrid construction of MnMoO4 nanorods anchored graphene nanosheets; an efficient electrocatalyst for the picomolar detection of ecological pollutant ornidazole in water and urine samples. Chemosphere. 2021 Jan 18;273:129665. doi: 10.1016/j.chemosphere.2021.129665. Epub ahead of print. PMID: 33508687. 7: Jin ZR, Fang D, Liu BH, Cai J, Tang WH, Jiang H, Xing GG. Roles of CatSper channels in the pathogenesis of asthenozoospermia and the therapeutic effects of acupuncture-like treatment on asthenozoospermia. Theranostics. 2021 Jan 1;11(6):2822-2844. doi: 10.7150/thno.51869. PMID: 33456575; PMCID: PMC7806476. 8: Chowdhury KH, Chowdhury MR, Mahmud S, Tareq AM, Hanif NB, Banu N, Reza ASMA, Emran TB, Simal-Gandara J. Drug Repurposing Approach against Novel Coronavirus Disease (COVID-19) through Virtual Screening Targeting SARS-CoV-2 Main Protease. Biology (Basel). 2020 Dec 23;10(1):2. doi: 10.3390/biology10010002. PMID: 33374717; PMCID: PMC7822464. 9: Guo BD, Zeng Y, Guo J, Han Q, Wang F, Yu GJ, Yan B, Liu SJ, Gao QH. [Mechanisms of Huanshao Capsules protecting the reproductive function in rats with ornidazole-induced asthenozoospermia]. Zhonghua Nan Ke Xue. 2020 May;26(5):446-451. Chinese. PMID: 33354955. 10: He S, Yin R, Lai T, Zhao Y, Guo W, Zhu M. Structure-dependent degradation of nitroimidazoles by cobalt-manganese layered double hydroxide catalyzed peroxymonosulfate process. Chemosphere. 2021 Mar;266:129006. doi: 10.1016/j.chemosphere.2020.129006. Epub 2020 Nov 18. PMID: 33239235. 11: Tunca AK, Karakaya D, Bulbul S. Developing and validation of impurity and the simultaneous quantity determination methods for tablet forms containing Ciprofloxacin HCl and Ornidazole. Pak J Pharm Sci. 2020 May;33(3):1105-1114. PMID: 33191235. 12: Sun Y, Sun X, Zhao L, Zhang Z, Wang Y, Dai Z, Zhao X, Pu X. DJ-1 deficiency causes metabolic abnormality in ornidazole-induced asthenozoospermia. Reproduction. 2020 Dec;160(6):931-941. doi: 10.1530/REP-20-0097. PMID: 33112771. 13: Nandy P, Mukherjee A, Pradhan C, Das S. Radio-Sensitizing Effects of CuII and ZnII Complexes of Ornidazole: Role of Nitro Radical Anion. ACS Omega. 2020 Oct 1;5(40):25668-25676. doi: 10.1021/acsomega.0c02811. PMID: 33073092; PMCID: PMC7557252. 14: Li B , Jiang YY , Sun YY , Wang YJ , Han ML , Wu YP , Ma LF , Li DS . The highly selective detecting of antibiotics and support of noble metal catalysts by a multifunctional Eu-MOF. Dalton Trans. 2020 Nov 3;49(42):14854-14862. doi: 10.1039/d0dt03176c. PMID: 33057509. 15: Wang MJ, DA Y, Zheng LC. [Study on the efficacy and safety of metronidazole combined with periodontal tissue regeneration in the treatment of periodontitis]. Shanghai Kou Qiang Yi Xue. 2020 Jun;29(3):293-297. Chinese. PMID: 33043347. 16: Bush N, Sharma V, Chandrahasan K, Patil AN. Ofloxacin-ornidazole fixed-dose combination medication-induced pancreatitis with positive rechallenge. J Family Med Prim Care. 2020 Jun 30;9(6):3157-3159. doi: 10.4103/jfmpc.jfmpc_531_20. PMID: 32984191; PMCID: PMC7491762. 17: Katti PA, Goundadkar BB. Azole pharmaceuticals induce germinal vesicle breakdown (GVBD) in preovulatory oocytes of zebrafish (Danio rerio): an in vitro study. Environ Sci Pollut Res Int. 2021 Jan;28(3):3694-3702. doi: 10.1007/s11356-020-10719-x. Epub 2020 Sep 14. PMID: 32929672. 18: Deniz-Sungur D, Aksel H, Karaismailoglu E, Sayin TC. The prescribing of antibiotics for endodontic infections by dentists in Turkey: a comprehensive survey. Int Endod J. 2020 Dec;53(12):1715-1727. doi: 10.1111/iej.13390. Epub 2020 Sep 18. PMID: 32805741. 19: Beyaz Ş, Akdeniz N, Yılmaz A, Demir S, Öztop N, Çolakoğlu B, Büyüköztürk S, Deniz G, Gelincik A. Diagnostic workup including CD203c-based basophil activation test in immediate hypersensitivity due to metronidazole and ornidazole and evaluation of cross-reactivity in between. Allergy. 2021 Mar;76(3):842-852. doi: 10.1111/all.14542. Epub 2020 Aug 27. PMID: 32761620. 20: Li Y, Xu Z, Qi H, Zhu Z, Chen S, Zhang G. Observation and Nursing of the Curative Effect of Ag/TiO₂ Nanomaterials on Bacterial Vaginosis and Trichomonal Vaginitis. J Nanosci Nanotechnol. 2020 Dec 1;20(12):7419-7424. doi: 10.1166/jnn.2020.18624. PMID: 32711609.

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