Rifabutin | CAS#72559-06-9 | broad-spectrum antibioti

MedKoo Cat#: 599103 | Name: Rifabutin

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Description:

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

Rifabutin is a broad-spectrum antibiotic that is being used as prophylaxis against disseminated Mycobacterium avium complex infection in HIV-positive patients.

Chemical Structure

Rifabutin

CAS#72559-06-9

Theoretical Analysis

MedKoo Cat#: 599103

Name: Rifabutin

CAS#: 72559-06-9

Chemical Formula: C46H62N4O11

Exact Mass: 846.4415

Molecular Weight: 847.01

Elemental Analysis: C, 65.23; H, 7.38; N, 6.61; O, 20.78

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
25mg	USD 550.00	2 Weeks

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Synonym

Rifabutin; LM-427; LM 427; LM427; Mycobutin; Rifabutina;

IUPAC/Chemical Name

Rifamycin XIV, 1',4-didehydro-1-deoxy-1,4-dihydro-5'-(2-methylpropyl)-1-oxo-

InChi Key

ATEBXHFBFRCZMA-NYGPAKPVSA-N

InChi Code

InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14+/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1

SMILES Code

O=C1c2c(O)c(C)c3c(C4=O)c2C5=NC6(CCN(CC(C)C)CC6)NC5=C1NC(/C(C)=C/C=C/[C@@H]([C@H](O)[C@H]([C@@H](O)[C@H]([C@@H]([C@H](C)[C@@H](OC)/C=C/O[C@]4(O3)C)OC(C)=O)C)C)C)=O

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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rifabutin is a semisynthetic ansamycin antibiotic with potent antimycobacterial properties. Rifabutin inhibits DNA-dependent RNA polymerase.

In vitro activity:

Mutations Asp516Val, Asp516Tyr, Leu533Pro and the double mutation Met515Ile and Leu533Pro influenced susceptibility to rifampicin, but not to rifabutin. All mutations at codons 531 and 526, except one isolate with a His526Cys mutation, correlated with resistance to both compounds. Reference: Clin Microbiol Infect. 2004 Jul;10(7):662-5. https://pubmed.ncbi.nlm.nih.gov/15214882/

In vivo activity:

The concomitant use of rifabutin and highly active antiretroviral therapy (HAART) can lead to successful treatment of HIV-infected patients with tuberculosis without increased side effects. Reference: Clin Infect Dis. 2000 May;30(5):779-83. https://pubmed.ncbi.nlm.nih.gov/10816148/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	118.06
	Ethanol	100.0	118.06

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 847.01 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

Formulation protocol:

1. Cavusoglu C, Karaca-Derici Y, Bilgic A. In-vitro activity of rifabutin against rifampicin-resistant Mycobacterium tuberculosis isolates with known rpoB mutations. Clin Microbiol Infect. 2004 Jul;10(7):662-5. doi: 10.1111/j.1469-0691.2004.00917.x. PMID: 15214882. 2. Nilles J, Weiss J, Sauter M, Haefeli WE, Ruez S, Theile D. Comprehensive in vitro analysis evaluating the variable drug-drug interaction risk of rifampicin compared to rifabutin. Arch Toxicol. 2023 Aug;97(8):2219-2230. doi: 10.1007/s00204-023-03531-2. Epub 2023 Jun 7. PMID: 37285043; PMCID: PMC10322781. 3. Narita M, Stambaugh JJ, Hollender ES, Jones D, Pitchenik AE, Ashkin D. Use of rifabutin with protease inhibitors for human immunodeficiency virus-infected patients with tuberculosis. Clin Infect Dis. 2000 May;30(5):779-83. doi: 10.1086/313771. Epub 2000 Apr 28. Erratum in: Clin Infect Dis 2000 Jun;30(6):992. PMID: 10816148. 4. Ramis IB, Figueiredo R, Ramos DF, Halicki PCB, von Groll A, Viveiros M, do Ceu Costa M, da Silva PEA. Activity of Rifabutin and Hemi-synthetic Derivatives Against Mycobacterium abscessus. Med Chem. 2018;14(4):394-399. doi: 10.2174/1573406414666171204102633. PMID: 29205119.

In vitro protocol:

In vivo protocol:

1. Narita M, Stambaugh JJ, Hollender ES, Jones D, Pitchenik AE, Ashkin D. Use of rifabutin with protease inhibitors for human immunodeficiency virus-infected patients with tuberculosis. Clin Infect Dis. 2000 May;30(5):779-83. doi: 10.1086/313771. Epub 2000 Apr 28. Erratum in: Clin Infect Dis 2000 Jun;30(6):992. PMID: 10816148. 2. Ramis IB, Figueiredo R, Ramos DF, Halicki PCB, von Groll A, Viveiros M, do Ceu Costa M, da Silva PEA. Activity of Rifabutin and Hemi-synthetic Derivatives Against Mycobacterium abscessus. Med Chem. 2018;14(4):394-399. doi: 10.2174/1573406414666171204102633. PMID: 29205119.

1: Min BJ, Seo ME, Bae JH, Kim JW, Kim JH. Development and validation of next- generation sequencing panel for personalized Helicobacter pylori eradication treatment targeting multiple species. Front Cell Infect Microbiol. 2024 Aug 29;14:1379790. doi: 10.3389/fcimb.2024.1379790. PMID: 39268485; PMCID: PMC11390507. 2: Tamr A, Kabbani D, Weinberger JJ. Rifabutin-Induced Thrombocytopenia in a Patient With Uncontrolled HIV: A Case Report. Cureus. 2024 Aug 6;16(8):e66339. doi: 10.7759/cureus.66339. PMID: 39247045; PMCID: PMC11377851. 3: Chin N, Smith LR, Gaudi S, Baldwin B. A Case of Multibacillary Borderline Lepromatous Leprosy in the United States Treated With Alternative Therapy. Cureus. 2024 Aug 6;16(8):e66275. doi: 10.7759/cureus.66275. PMID: 39238714; PMCID: PMC11376142. 4: Lewis JH, Korkmaz SY, Rizk CA, Copeland MJ. Diagnosis, prevention and risk- management of drug-induced liver injury due to medications used to treat mycobacterium tuberculosis. Expert Opin Drug Saf. 2024 Sep 4:1-15. doi: 10.1080/14740338.2024.2399074. Epub ahead of print. PMID: 39212296. 5: Graham DY, Naser SA, Borody T, Hebzda Z, Sarles H, Levenson S, Hardi R, Arłukowicz T, Svorcan P, Fathi R, Bibliowicz A, Anderson P, McLean P, Fehrmann C, Harris MS, Zhao S, Kalfus IN. Randomized, Double-Blind, Placebo-Controlled Study of Anti-Mycobacterial Therapy (RHB-104) in Active Crohn's Disease. Antibiotics (Basel). 2024 Jul 25;13(8):694. doi: 10.3390/antibiotics13080694. PMID: 39199994; PMCID: PMC11350828. 6: Yuan M, Dong G, Han N, Yan L, Tang H. Disseminated Mycobacterium tilburgii infection in a person with AIDS: A case report. Heliyon. 2024 Aug 2;10(15):e35616. doi: 10.1016/j.heliyon.2024.e35616. PMID: 39170256; PMCID: PMC11336850. 7: Sapkota A, Park EJ, Kim YJ, Heo JB, Nguyen TQ, Heo BE, Kim JK, Lee SH, Kim SI, Choi YJ, Roh T, Jeon SM, Jang M, Heo HJ, Whang J, Paik S, Yuk JM, Kim JM, Song GY, Jang J, Jo EK. The autophagy-targeting compound V46 enhances antimicrobial responses to Mycobacteroides abscessus by activating transcription factor EB. Biomed Pharmacother. 2024 Aug 20;179:117313. doi: 10.1016/j.biopha.2024.117313. Epub ahead of print. PMID: 39167844. 8: Yusuf B, Wang S, Alam MS, Zhang J, Liu Z, Lu Z, Ding J, Chiwala G, Gao Y, Fang C, Khan SA, Tian X, Islam MM, Hameed HMA, Maslov DA, Zhong N, Hu J, Zhang T. Investigating the role of MAB_1915 in intrinsic resistance to multiple drugs in Mycobacterium abscessus. Microbiol Spectr. 2024 Aug 20:e0397423. doi: 10.1128/spectrum.03974-23. Epub ahead of print. PMID: 39162545. 9: Yan J, Zheng R, Zhang Z, Shi J, Yan T, Liu H, Li F. Swollen Necrotic Lymphadenitis Infected with Mycobacterium Paracondontium in an AIDS Patient: a Case Report and Literature Review. Infect Drug Resist. 2024 Aug 9;17:3475-3482. doi: 10.2147/IDR.S473762. PMID: 39139625; PMCID: PMC11321343. 10: Wang Z, Beugnies E, Rachdi M, Makhoul D, Leys E, Le A. Rifabutin-induced uveitis: A jellyfish in the eye. J Fr Ophtalmol. 2024 Aug 12:104266. doi: 10.1016/j.jfo.2024.104266. Epub ahead of print. PMID: 39138045. 11: Deshpande D, Magombedze G, Srivastava S, Gumbo T. Antibacterial action of penicillin against Mycobacterium avium complex. IJTLD Open. 2024 Aug 1;1(8):362-368. doi: 10.5588/ijtldopen.24.0238. PMID: 39131587; PMCID: PMC11308404. 12: Lin WH, Yao C, Mei L, Wang DP, Bao XD, Liu SS. Screening, epidemic trends and drug sensitivity analysis of nontuberculous mycobacteria in a local area of China. Am J Transl Res. 2024 Jul 15;16(7):3298-3305. doi: 10.62347/MAJY5046. PMID: 39114690; PMCID: PMC11301460. 13: Mann L, Siersleben F, Lang M, Richter A. Determination of bactericidal activity against 3HC-2-Tre-labelled Mycobacterium abscessus (Mycobacteroides abscessus) by automated fluorescence microscopy. J Microbiol Methods. 2024 Sep;224:107002. doi: 10.1016/j.mimet.2024.107002. Epub 2024 Jul 20. PMID: 39038561. 14: Semere Gebreyesus M, Wasmann RE, McIlleron H, Oladokun R, Okonkwo P, Wiesner L, Denti P, Rawizza HE. Population pharmacokinetics of rifabutin among HIV/TB co-infected children on lopinavir/ritonavir-based antiretroviral therapy. Antimicrob Agents Chemother. 2024 Aug 7;68(8):e0035424. doi: 10.1128/aac.00354-24. Epub 2024 Jul 22. PMID: 39037240; PMCID: PMC11304744. 15: Wasserman S, Antilus-Sainte R, Abdelgawad N, Odjourian NM, Cristaldo M, Dougher M, Kaya F, Zimmerman M, Denti P, Gengenbacher M. Rifabutin central nervous system concentrations in a rabbit model of tuberculous meningitis. Antimicrob Agents Chemother. 2024 Aug 7;68(8):e0078324. doi: 10.1128/aac.00783-24. Epub 2024 Jul 19. PMID: 39028192; PMCID: PMC11304741. 16: Kim Y, Bae S, Huh KY, Joo JS, Lee J, Song SH, Yu KS, Jang IJ, Oh J. Coadministration of Voriconazole and Rifabutin Can Increase the Risk of Adverse Drug Reactions in Patients with Multiple Infections. Ther Drug Monit. 2024 Jul 16. doi: 10.1097/FTD.0000000000001241. Epub ahead of print. PMID: 39023363. 17: Ahmad F, Ahmad S, Upadhyay TK, Singh S, Khubaib M, Singh J, Saeed M, Ahmad I, Al-Keridis LA, Sharma R. Rifabutin loaded inhalable β-glucan microparticle based drug delivery system for pulmonary TB. Sci Rep. 2024 Jul 16;14(1):16437. doi: 10.1038/s41598-024-66634-5. PMID: 39013991; PMCID: PMC11253001. 18: Sue S, Ikeda R, Ikeda A, Sato H, Kaneko H, Irie K, Maeda S. Single-Arm, Prospective, Interventional Study of Helicobacter pylori Eradication Rescue Therapy with Rifabutin, Metronidazole, and Vonoprazan. J Clin Med. 2024 Jun 27;13(13):3774. doi: 10.3390/jcm13133774. PMID: 38999340; PMCID: PMC11242301. 19: Mangat R, Brode SK, Mah HK, Brar MS, Sabur NF. Characteristics of and treatment outcomes in rifampicin-intolerant patients. IJTLD Open. 2024 Apr 1;1(4):160-165. doi: 10.5588/ijtldopen.23.0466. PMID: 38988405; PMCID: PMC11231820. 20: Guo CG, Jiang F, Li Y, Chen Y, Wu J, Zhang S, Leung WK. Real-world efficacy of second-line therapies for Helicobacter pylori: a population-based study. J Antimicrob Chemother. 2024 Sep 3;79(9):2263-2272. doi: 10.1093/jac/dkae224. PMID: 38973619.