Bucillamine | CAS#65002-17-7 | antirheumatic

MedKoo Cat#: 315351 | Name: Bucillamine

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Description:

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

Bucillamine is an antirheumatic agent developed from tiopronin. It is mainly used in Japan and Korea. Activity is mediated by the two thiol groups that the molecule contains. Research done in USA showed positive transplant preservation properties.

Chemical Structure

Bucillamine

CAS#65002-17-7

Theoretical Analysis

MedKoo Cat#: 315351

Name: Bucillamine

CAS#: 65002-17-7

Chemical Formula: C7H13NO3S2

Exact Mass: 223.0337

Molecular Weight: 223.31

Elemental Analysis: C, 37.65; H, 5.87; N, 6.27; O, 21.49; S, 28.72

Price and Availability

Size	Price	Availability
25mg	USD 285.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
250mg	USD 1,250.00	2 Weeks
500mg	USD 1,950.00	2 Weeks

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Related CAS #

82017-48-9 (disuflide)

Synonym

Bucillamine; DE-019; DE 019; DE019; SA96; Thiobutarit; Tiobutarit; Rimatil.

IUPAC/Chemical Name

3-mercapto-2-(2-mercapto-2-methylpropanamido)propanoic acid

InChi Key

VUAFHZCUKUDDBC-UHFFFAOYSA-N

InChi Code

InChI=1S/C7H13NO3S2/c1-7(2,13)6(11)8-4(3-12)5(9)10/h4,12-13H,3H2,1-2H3,(H,8,11)(H,9,10)

SMILES Code

O=C(O)C(NC(C(C)(S)C)=O)CS

Appearance

solid powder

Purity

>97% (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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

In vitro activity:

Results showed that the addition of bucillamine restored EGFR autophosphorylation and reactivated AKT and ERK1/2 partially, indicating that bucillamine attenuates afatinib-mediated inhibition of EGFR signaling in human cells. Reference: Pharmaceuticals (Basel). 2019 Dec; 12(4): 165. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6958386/

In vivo activity:

However, bucillamine pretreatment suppressed UVB-mediated MAPK activation compared to saline treatment at the same time points. For examples, bucillamine reduced JNK phosphorylation at 6 and 12 h post UVB irradiation when compared to UVB alone-treated mice, and reduced UVB-induced ERK phosphorylation at 12 and 24 h when compared to saline-treated controls. At 24 h time point, bucillamine also reduced UVB-induced p38 phosphorylation when compared to the saline-treated counterparts (Figure 3a–c). These data suggest that bucillamine at pharmacological doses protects against the activation of MAPK signaling in UVB-exposed mouse skin. Reference: Photochem Photobiol. 2020 Jul; 96(4): 870–876. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7387142/

Preparing Stock Solutions

The following data is based on the product molecular weight 223.31 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. Anwar A, Anwar H, Yamauchi T, Tseng R, Agarwal R, Horwitz LD, Zhai Z, Fujita M. Bucillamine Inhibits UVB-Induced MAPK Activation and Apoptosis in Human HaCaT Keratinocytes and SKH-1 Hairless Mouse Skin. Photochem Photobiol. 2020 Jul;96(4):870-876. doi: 10.1111/php.13228. Epub 2020 Apr 13. PMID: 32077107; PMCID: PMC7387142. 2. Nishiya N, Murai M, Hosoda A, Yonezawa H, Omori N. Bucillamine Prevents Afatinib-Mediated Inhibition of Epidermal Growth Factor Receptor Signaling. Pharmaceuticals (Basel). 2019 Nov 7;12(4):165. doi: 10.3390/ph12040165. PMID: 31703435; PMCID: PMC6958386.

In vitro protocol:

In vivo protocol:

1: Horwitz LD. Bucillamine: a potent thiol donor with multiple clinical applications. Cardiovasc Drug Rev. 2003 Summer;21(2):77-90. doi: 10.1111/j.1527-3466.2003.tb00107.x. PMID: 12847560. 2: Nakamoto K, Tanaka Y, Sasaki Y, Goto H. Bucillamine-induced interstitial pneumonitis. J Gen Fam Med. 2018 Mar 30;19(3):111-112. doi: 10.1002/jgf2.169. PMID: 29744266; PMCID: PMC5931345. 3: Yanagishita T, Tamada Y, Watanabe D. Bucillamine-induced pemphigus vulgaris. J Eur Acad Dermatol Venereol. 2015 Jun;29(6):1242-3. doi: 10.1111/jdv.12472. Epub 2014 Mar 18. PMID: 24641261. 4: Mori T, Yokogawa N, Higuchi R, Tsujino M, Shimada K, Sugii S. Bucillamine- induced gigantomastia with galactorrhea and hyperprolactinaemia. Mod Rheumatol Case Rep. 2020 Jan;4(1):122-125. doi: 10.1080/24725625.2019.1673939. Epub 2019 Oct 14. PMID: 33086961. 5: Nakagomi D, Ikeda K, Hirotoshi K, Kobayashi Y, Suto A, Nakajima H. Bucillamine-induced yellow nail in Japanese patients with rheumatoid arthritis: two case reports and a review of 36 reported cases. Rheumatol Int. 2013 Mar;33(3):793-7. doi: 10.1007/s00296-011-2241-z. Epub 2011 Nov 17. Erratum in: Rheumatol Int. 2013 Oct;33(10):2707. Kawashima, Hironori [corrected to Hirotoshi, Kawashima]. PMID: 22090009. 6: Anwar A, Anwar H, Yamauchi T, Tseng R, Agarwal R, Horwitz LD, Zhai Z, Fujita M. Bucillamine Inhibits UVB-Induced MAPK Activation and Apoptosis in Human HaCaT Keratinocytes and SKH-1 Hairless Mouse Skin. Photochem Photobiol. 2020 Jul;96(4):870-876. doi: 10.1111/php.13228. Epub 2020 Apr 13. PMID: 32077107; PMCID: PMC7387142. 7: Frank M. Bucillamine in the treatment of patients with mild to moderate COVID-19: an interview with Michael Frank. Future Microbiol. 2022 Feb;17(3):157-159. doi: 10.2217/fmb-2021-0277. Epub 2022 Jan 19. PMID: 35044238; PMCID: PMC8787611. 8: Kim SJ, Ho Hur J, Park C, Kim HJ, Oh GS, Lee JN, Yoo SJ, Choe SK, So HS, Lim DJ, Moon SK, Park R. Bucillamine prevents cisplatin-induced ototoxicity through induction of glutathione and antioxidant genes. Exp Mol Med. 2015 Feb 20;47(2):e142. doi: 10.1038/emm.2014.112. PMID: 25697147; PMCID: PMC4346486. 9: Izumi A, Katsumi S, Kobayashi N, Niizeki H, Asada H, Miyagawa S. Bucillamine- induced toxic epidermal necrolysis and fixed drug eruption. J Dermatol. 2005 May;32(5):397-401. doi: 10.1111/j.1346-8138.2005.tb00914.x. PMID: 16043905. 10: Tanizaki R, Hashimoto S, Takemura Y. Bucillamine-induced yellow nail syndrome. J Gen Fam Med. 2017 Aug 29;18(6):479-480. doi: 10.1002/jgf2.124. PMID: 29264101; PMCID: PMC5729360. 11: Kurashima K, Nakao S, Fujimura M, Matsuda T. Bucillamine-induced hypersensitivity pneumonitis. Chest. 1992 May;101(5):1479-80. doi: 10.1378/chest.101.5.1479-c. PMID: 1582337. 12: Takeda T, Shimizu Y, Takeuchi M, Hashimoto S, Nagai C, Uchiyama S, Iwata M. [Bucillamine-induced dermatomyositis-like clinical features in a patient with rheumatoid arthritis]. Rinsho Shinkeigaku. 2005 Jan;45(1):45-8. Japanese. PMID: 15715001. 13: Nishiya N, Murai M, Hosoda A, Yonezawa H, Omori N. Bucillamine Prevents Afatinib-Mediated Inhibition of Epidermal Growth Factor Receptor Signaling. Pharmaceuticals (Basel). 2019 Nov 7;12(4):165. doi: 10.3390/ph12040165. PMID: 31703435; PMCID: PMC6958386. 14: Isozaki T, Kimura M, Ikegaya N, Arai T, Fujigaki Y, Hishida A, Kaneko E. Bucillamine (a new therapeutic agent for rheumatoid arthritis) induced nephrotic syndrome: a report of two cases and review of the literature. Clin Investig. 1992 Nov;70(11):1036-42. doi: 10.1007/BF00180315. PMID: 1472834. 15: Takamatsu N, Takizawa H, Sugawara H, Ogawa Y. Acute interstitial nephritis with membranous nephropathy in bucillamine-treated rheumatoid arthritis. CEN Case Rep. 2016 May;5(1):103-107. doi: 10.1007/s13730-015-0204-z. Epub 2015 Dec 8. PMID: 28509179; PMCID: PMC5411667. 16: Amersi F, Nelson SK, Shen XD, Kato H, Melinek J, Kupiec-Weglinski JW, Horwitz LD, Busuttil RW, Horwitz MA. Bucillamine, a thiol antioxidant, prevents transplantation-associated reperfusion injury. Proc Natl Acad Sci U S A. 2002 Jun 25;99(13):8915-20. doi: 10.1073/pnas.132026099. PMID: 12084933; PMCID: PMC124398. 17: Horwitz LD, Sherman NA. Bucillamine prevents myocardial reperfusion injury. J Cardiovasc Pharmacol. 2001 Dec;38(6):859-67. doi: 10.1097/00005344-200112000-00007. PMID: 11707689. 18: Wielandt AM, Vollrath V, Farias M, Chianale J. Bucillamine induces glutathione biosynthesis via activation of the transcription factor Nrf2. Biochem Pharmacol. 2006 Aug 14;72(4):455-62. doi: 10.1016/j.bcp.2006.05.011. Epub 2006 Jun 27. PMID: 16806086. 19: Manabe S, Banno M, Nakano M, Fujii T, Fujiwara M, Kita Y, Nitta K, Hatano M. Bucillamine-induced membranous nephropathy with crescent formation in a patient with rheumatoid arthritis: case report and literature review. Case Rep Nephrol Dial. 2014 Oct 29;5(1):30-8. doi: 10.1159/000368826. PMID: 25849672; PMCID: PMC4294451. 20: Nagahama K, Matsushita H, Hara M, Ubara Y, Hara S, Yamada A. Bucillamine induces membranous glomerulonephritis. Am J Kidney Dis. 2002 Apr;39(4):706-12. doi: 10.1053/ajkd.2002.31987. PMID: 11920335.