Ascomycin | CAS#104987-12-4 | immunosuppressant

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

MedKoo CAT#: 326707

CAS#: 104987-12-4

Description: Ascomycin, also known as KF-520, FR900520, L 683590, produced by the fermentation of S. hygroscopicus subsp. ascomyceticus, is an ethyl analog of tacrolimus (FK-506) with potent immunosuppressant properties.

Chemical Structure

Ascomycin

CAS# 104987-12-4

Instruction

Theoretical Analysis

MedKoo Cat#: 326707
Name: Ascomycin
CAS#: 104987-12-4
Chemical Formula: C43H69NO12
Exact Mass: 791.48
Molecular Weight: 792.020
Elemental Analysis: C, 65.21; H, 8.78; N, 1.77; O, 24.24

Price and Availability

Size	Price	Availability
100mg	USD 250	2 Weeks
200mg	USD 450	2 Weeks
500mg	USD 950	2 Weeks
1g	USD 1650	2 Weeks
2g	USD 2950	2 Weeks
5g	USD 5850	2 Weeks
10g	USD 8950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: FK-520; FK-520; FK-520; FR900520; FR-900520; FR-900520; L 683590; L-683590; L683590; Changchuanmycin; Immunomycin. Ascomycin

IUPAC/Chemical Name: (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone

InChi Key: ZDQSOHOQTUFQEM-NURRSENYSA-N

InChi Code: InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32+,33-,35+,36-,37-,38+,39+,43+/m0/s1

SMILES Code: O=C([C@@](CCCC1)([H])N1C(C([C@@]2(O)[C@H](C)C[C@H](OC)[C@@](O2)([H])[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H]3CC)=O)=O)O[C@H](/C(C)=C/[C@H]4C[C@@H](OC)[C@H](O)CC4)[C@H](C)[C@@H](O)CC3=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, not in water

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

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 792.02 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:
In vitro protocol:
In vivo protocol:

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1: Qi H, Zhao S, Fu H, Wen J, Jia X. Enhancement of ascomycin production in Streptomyces hygroscopicus var. ascomyceticus by combining resin HP20 addition and metabolic profiling analysis. J Ind Microbiol Biotechnol. 2014 Sep;41(9):1365-74. doi: 10.1007/s10295-014-1473-9. Epub 2014 Jun 26. PubMed PMID: 24965502.

2: Bulusu MA, Baumann K, Stuetz A. Chemistry of the immunomodulatory macrolide ascomycin and related analogues. Prog Chem Org Nat Prod. 2011;94:59-126. doi: 10.1007/978-3-7091-0748-5_2. Review. PubMed PMID: 21833838.

3: Sierra-Paredes G, Sierra-Marcuño G. Ascomycin and FK506: pharmacology and therapeutic potential as anticonvulsants and neuroprotectants. CNS Neurosci Ther. 2008 Spring;14(1):36-46. doi: 10.1111/j.1527-3458.2008.00036.x. Review. PubMed PMID: 18482098.

4: Vázquez-López A, Sierra-Paredes G, Sierra-Marcuño G. Anticonvulsant effect of the calcineurin inhibitor ascomycin on seizures induced by picrotoxin microperfusion in the rat hippocampus. Pharmacol Biochem Behav. 2006 Jul;84(3):511-6. Epub 2006 Jul 26. PubMed PMID: 16872668.

5: Napoli KL. Organic solvents compromise performance of internal standard (ascomycin) in proficiency testing of mass spectrometry-based assays for tacrolimus. Clin Chem. 2006 Apr;52(4):765-6. PubMed PMID: 16595827.

6: Junker J, Maier W, Lindel T, Köck M. Computer-assisted constitutional assignment of large molecules: COCON analysis of ascomycin. Org Lett. 1999 Sep 9;1(5):737-40. PubMed PMID: 16118875.

7: Monaghan P, Fardis M, Revill WP, Bell A. Antimalarial effects of macrolactones related to FK520 (ascomycin) are independent of the immunosuppressive properties of the compounds. J Infect Dis. 2005 Apr 15;191(8):1342-9. Epub 2005 Mar 4. PubMed PMID: 15776382.

8: Revill WP, Voda J, Reeves CR, Chung L, Schirmer A, Ashley G, Carney JR, Fardis M, Carreras CW, Zhou Y, Feng L, Tucker E, Robinson D, Gold BG. Genetically engineered analogs of ascomycin for nerve regeneration. J Pharmacol Exp Ther. 2002 Sep;302(3):1278-85. PubMed PMID: 12183690.

9: Uchida T, Fujimori F, Nagata N. Identification of genes coding enzymes for ascomycin tetra-hydropyranose ring formation. Int J Mol Med. 2002 Feb;9(2):141-5. PubMed PMID: 11786924.

10: Reeves CD, Chung LM, Liu Y, Xue Q, Carney JR, Revill WP, Katz L. A new substrate specificity for acyl transferase domains of the ascomycin polyketide synthase in Streptomyces hygroscopicus. J Biol Chem. 2002 Mar 15;277(11):9155-9. Epub 2002 Jan 10. PubMed PMID: 11786554.

11: Song Z, DeMarco A, Zhao M, Corley EG, Thompson AS, McNamara J, Li Y, Rieger D, Sohar P, Mathre DJ, Tschaen DM, Reamer RA, Huntington MF, Ho GJ, Tsay FR, Emerson K, Shuman R, Grabowski EJ, Reider PJ. Highly Chemoselective Trichloroacetimidate-Mediated Alkylation of Ascomycin: A Convergent, Practical Synthesis of the Immunosuppressant L-733,725. J Org Chem. 1999 Mar 19;64(6):1859-1867. PubMed PMID: 11674275.

12: Zuberbier T, Chong SU, Grunow K, Guhl S, Welker P, Grassberger M, Henz BM. The ascomycin macrolactam pimecrolimus (Elidel, SDZ ASM 981) is a potent inhibitor of mediator release from human dermal mast cells and peripheral blood basophils. J Allergy Clin Immunol. 2001 Aug;108(2):275-80. PubMed PMID: 11496246.

13: Griffiths CE. Ascomycin: an advance in the management of atopic dermatitis. Br J Dermatol. 2001 Apr;144(4):679-81. PubMed PMID: 11298524.

14: Queille-Roussel C, Paul C, Duteil L, Lefebvre MC, Rapatz G, Zagula M, Ortonne JP. The new topical ascomycin derivative SDZ ASM 981 does not induce skin atrophy when applied to normal skin for 4 weeks: a randomized, double-blind controlled study. Br J Dermatol. 2001 Mar;144(3):507-13. PubMed PMID: 11260007.

15: Küsters E, Heuer C, Wieckhusen D. Purification of an ascomycin derivative with simulated moving bed chromatography. A case study. J Chromatogr A. 2000 Apr 7;874(2):155-65. PubMed PMID: 10817355.

16: Wiedeman PE, Fesik SW, Petros AM, Nettesheim DG, Mollison KW, Lane BC, Or YS, Luly JR. Retention of immunosuppressant activity in an ascomycin analogue lacking a hydrogen-bonding interaction with FKBP12. J Med Chem. 1999 Oct 21;42(21):4456-61. PubMed PMID: 10543889.

17: Armstrong HM, Wong F, Holmes MA, Sinclair PJ, Goulet MT, Dumont FJ, Staruch MJ, Koprak S, Peterson LB, Rosa R, Wilusz MB, Wiederrecht GJ, Cryan JG, Wyvratt MJ, Parsons WH. Potent immunosuppressive C32-O-arylethyl ether derivatives of ascomycin with reduced toxicity. Bioorg Med Chem Lett. 1999 Jul 19;9(14):2089-94. PubMed PMID: 10450987.

18: Goulet MT, Sinclair PJ, Wong F, Staruch MJ, Dumont FJ, Cryan JG, Wiederrecht GJ, Wyvratt MJ, Parsons WH. C32-O-phenalkyl ether derivatives of the immunosuppressant ascomycin: a tether length study. Bioorg Med Chem Lett. 1999 Jul 19;9(14):2085-8. PubMed PMID: 10450986.

19: Becker JW, Rotonda J, Cryan JG, Martin M, Parsons WH, Sinclair PJ, Wiederrecht G, Wong F. 32-Indolyl ether derivatives of ascomycin: three-dimensional structures of complexes with FK506-binding protein. J Med Chem. 1999 Jul 29;42(15):2798-804. PubMed PMID: 10425089.

20: Mollison KW, Fey TA, Gauvin DM, Sheets MP, Smith ML, Pong M, Krause R, Miller L, Or YS, Kawai M, Wagner R, Wiedeman PE, Clark RF, Gunawardana IW, Rhoades TA, Henry CL, Tu NP, BaMaung NY, Kopecka H, Liu L, Xie Q, Lane BC, Trevillyan JM, Marsh K, Luly JR, et al. Discovery of ascomycin analogs with potent topical but weak systemic activity for treatment of inflammatory skin diseases. Curr Pharm Des. 1998 Oct;4(5):367-79. Review. PubMed PMID: 10197049.

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