Tigecycline | CAS#220620-09-7 | glycylcycline antibiotic

MedKoo Cat#: 315297 | Name: Tigecycline

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Description:

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

Tigecycline is a glycylcycline antibiotic developed by Francis Tally and marketed by Wyeth under the brand name Tygacil. It was given a U.S. Food and Drug Administration (FDA) fast-track approval and was approved on June 17, 2005. It was developed in response to the growing prevalence of antibiotic resistance in bacteria such as Staphylococcus aureus and Acinetobacter baumannii. The New Delhi metallo-β-Lactamase multidrug-resistant Enterobacteriaceae has also shown susceptibility to tigecycline.

Chemical Structure

Tigecycline

CAS#220620-09-7

Theoretical Analysis

MedKoo Cat#: 315297

Name: Tigecycline

CAS#: 220620-09-7

Chemical Formula: C29H39N5O8

Exact Mass: 585.2799

Molecular Weight: 585.65

Elemental Analysis: C, 59.47; H, 6.71; N, 11.96; O, 21.86

Price and Availability

Size	Price	Availability
100mg	USD 350.00
500mg	USD 750.00	2 Weeks
1g	USD 950.00	2 Weeks
2g	USD 1,650.00	2 Weeks
5g	USD 2,650.00	2 Weeks

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Related CAS #

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Synonym

GAR936; GAR-936; GAR936; Tigecycline; trade name: TYGACL.

IUPAC/Chemical Name

(4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

InChi Key

FPZLLRFZJZRHSY-HJYUBDRYSA-N

InChi Code

InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1

SMILES Code

O=C(C1=C(O)[C@@H](N(C)C)[C@@](C[C@@]2([H])C(C(C3=C(O)C(NC(CNC(C)(C)C)=O)=CC(N(C)C)=C3C2)=O)=C4O)([H])[C@@]4(O)C1=O)N

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

>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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 585.65 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

1: Jo J, Kim SJ, Kwon KT, Ko KS. Resilience of tigecycline heteroresistance phenotype in Acinetobacter baumannii. J Antimicrob Chemother. 2024 Dec 4:dkae436. doi: 10.1093/jac/dkae436. Epub ahead of print. PMID: 39656811. 2: Wei Z, Xu J, Wu J, Wang Y, Chen S. Phenotypic Profiling of Tigecycline- resistant Klebsiella pneumoniae Strains Induced In vitro. Curr Microbiol. 2024 Dec 13;82(1):37. doi: 10.1007/s00284-024-04018-8. PMID: 39671135. 3: Sun P, Jian J, Chen L. Distribution and Drug Resistance of Pathogens of Catheter-Related Blood Stream Infection in a Hospital from 2017 to 2021. Clin Lab. 2024 Dec 1;70(12). doi: 10.7754/Clin.Lab.2024.240514. PMID: 39661995. 4: Almoghrabi Y, Daghistani H, Niyazi HA, Niyazi HA, AbdulMajed H, Juma NA, Daffa N, Helmi NR, Al-Rabia MW, Mokhtar JA, Saleh BH, Attallah DM, Matar M, Shukri HA, Moqaddam SA, Alamoudi S, Alkuwaity KK, Abujamel T, Sait AM, Mufrrih M, Al-Zahrani IA, O'hagan S, Ismail MA, Alharbi OS, Momin HJ, Abu IM, Alfadil A, Ibrahem K. Epidemiological and Clinical Insights into Acinetobacter baumannii: A Six-Year Study on Age, Antibiotics, and Specimens. Int J Gen Med. 2024 Dec 3;17:5715-5725. doi: 10.2147/IJGM.S489514. PMID: 39650788; PMCID: PMC11625184. 5: Liu JJ, Guo DD, Wang MX, Li YZ, Li H, Liu SB, Yang RL, Zhang DH. Efficacy and safety of eravacycline versus tigecycline for complicated intra-abdominal infections in the ICU: a multicenter, single-blind, parallel randomized controlled trial study protocol. Front Med (Lausanne). 2024 Nov 22;11:1496402. doi: 10.3389/fmed.2024.1496402. PMID: 39650187; PMCID: PMC11620859. 6: Wang C, Luo B, Liu W, Jia C, Chen H, Ma J, Song X, Ji X, Cao A, Bai Y, Qiu W. Development and clinical utility of an ultra performance liquid chromatography - tandem mass spectrometry assay for monitoring omadacycline and tigecycline in severe bacterial infections. J Mass Spectrom Adv Clin Lab. 2024 Nov 22;34:46-54. doi: 10.1016/j.jmsacl.2024.11.001. PMID: 39649553; PMCID: PMC11625210. 7: Huang CF, Yang JL, Chuang YC, Sheng WH. Evaluating Risk Factors for Clinical Failure Among Tigecycline-Treated Patients. Infect Drug Resist. 2024 Dec 4;17:5387-5393. doi: 10.2147/IDR.S496809. PMID: 39649431; PMCID: PMC11625427. 8: Wang Z, Li H. The tigecycline resistance mechanisms in Gram-negative bacilli. Front Cell Infect Microbiol. 2024 Nov 20;14:1471469. doi: 10.3389/fcimb.2024.1471469. PMID: 39635040; PMCID: PMC11615727. 9: Su W, Wang W, Li L, Zhang M, Xu H, Fu C, Pang X, Wang M. Mechanisms of tigecycline resistance in Gram-negative bacteria: A narrative review. Eng Microbiol. 2024 Aug 17;4(3):100165. doi: 10.1016/j.engmic.2024.100165. PMID: 39629109; PMCID: PMC11610970. 10: Anjum A, Tabassum J, Islam S, Hassan AKMI, Jabeen I, Shuvo SR. Deciphering the genomic character of the multidrug-resistant Staphylococcus aureus from Dhaka, Bangladesh. AIMS Microbiol. 2024 Sep 29;10(4):833-858. doi: 10.3934/microbiol.2024036. PMID: 39628721; PMCID: PMC11609420. 11: Attalla ET, Khalil AM, Zakaria AS, Evans R, Tolba NS, Mohamed NM. Efficacy of colistin-based combinations against pandrug-resistant whole-genome-sequenced Klebsiella pneumoniae isolated from hospitalized patients in Egypt: an in vitro/vivo comparative study. Gut Pathog. 2024 Dec 3;16(1):73. doi: 10.1186/s13099-024-00667-z. PMID: 39627871; PMCID: PMC11616336. 12: Bai H, Zhang J, Li S, Lu M, Li J, Li R. Electrocatalytic study on the degradation of tigecycline wastewater using a three-dimensional porous agarose@MXene hydrogel carbon cloth electrode with high conductivity. Int J Biol Macromol. 2024 Dec 1;285:138231. doi: 10.1016/j.ijbiomac.2024.138231. Epub ahead of print. PMID: 39626821. 13: García P, Guijarro-Sánchez P, Lasarte-Monterrubio C, Muras A, Alonso-García I, Outeda-García M, Maceiras R, Fernández-López MDC, Rodríguez-Coello A, García- Pose A, Blanco-Martín T, González-Pinto L, Arca-Suárez J, Vázquez-Ucha JC, Bou G, Beceiro A; Spanish National Acinetobacter spp. 2020 Study Group and GEMARA- SEIMC/REIPI Enterobacterales Study Group. Activity and resistance mechanisms of the third generation tetracyclines tigecycline, eravacycline and omadacycline against nationwide Spanish collections of carbapenemase-producing Enterobacterales and Acinetobacter baumannii. Biomed Pharmacother. 2024 Dec 2;181:117666. doi: 10.1016/j.biopha.2024.117666. Epub ahead of print. PMID: 39626376. 14: Liao X, Liang Q, Dai X, Wu S, Duan C, Luo Z, Xie X. In vitro activities of eravacycline against clinical bacterial isolates: a multicenter study in Guangdong, China. Front Microbiol. 2024 Nov 18;15:1504013. doi: 10.3389/fmicb.2024.1504013. PMID: 39624714; PMCID: PMC11609169. 15: Foysal MJ, Momtaz F, Chowdhury AMMA, Tanni AA, Salauddin A, Hasan MZ, Mina SA, Sultana N, Biswas SK, Islam K, Tay A, Mannan A. Whole-Genome Analysis of Multidrug-Resistant Klebsiella pneumoniae Kp04 Reveals Distinctive Antimicrobial and Arsenic-Resistance Genomic Features: A Case Study from Bangladesh. Curr Microbiol. 2024 Nov 29;82(1):22. doi: 10.1007/s00284-024-03996-z. PMID: 39613891. 16: Guo W, Lin Q, Li J, Feng X, Zhen S, Mi Y, Zheng Y, Zhang F, Xiao Z, Jiang E, Han M, Wang J, Feng S. Stenotrophomonas maltophilia bacteremia in adult patients with hematological diseases: clinical characteristics and risk factors for 28-day mortality. Microbiol Spectr. 2024 Nov 29:e0101124. doi: 10.1128/spectrum.01011-24. Epub ahead of print. PMID: 39611832. 17: Zhong FL, He JJ, Bai KH, Shao RN, Wu GY, Tian XP, Wang DW, Dai YJ, Chen SL. Tigecycline-induced coagulation gene prognostic prediction model and intestinal flora signature in AML. Front Immunol. 2024 Nov 14;15:1486592. doi: 10.3389/fimmu.2024.1486592. PMID: 39611150; PMCID: PMC11602473. 18: Waheed F, Khan AS, Babar U, Khan MS. SURGICAL SITE INFECTION WITH EXTREME DRUG-RESISTANT ACINETOBACTER BAUMANII: A WAKE-UP CALL! J Ayub Med Coll Abbottabad. 2024 Apr-Jun;36(2):430-432. doi: 10.55519/JAMC-02-12363. PMID: 39609995. 19: Fang R, Di L, Tian X, Bai Y. Genomic and phylogenetic analysis of a NDM-1 producing ST152 Klebsiella pneumoniae isolated from a bloodstream infection in China. J Glob Antimicrob Resist. 2024 Nov 27;40:34-36. doi: 10.1016/j.jgar.2024.11.005. Epub ahead of print. PMID: 39608707. 20: Tarski I, Śmiechowicz J, Duszyńska W. Cefiderocol in the Successful Treatment of Complicated Hospital-Acquired K. pneumoniae NDM, OXA48 Intraabdominal Infection. Infect Drug Resist. 2024 Nov 23;17:5163-5170. doi: 10.2147/IDR.S485450. PMID: 39605990; PMCID: PMC11600933.