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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H69NO12
Molecular Weight 792.0091
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ASCOMYCIN

SMILES

CC[C@]1([H])/C(/[H])=C(\C)/C[C@]([H])(C)C[C@@]([H])([C@]2([H])[C@]([H])(C[C@@]([H])(C)[C@@](C(=O)C(=O)N3CCCC[C@@]3([H])C(=O)O[C@]([H])(/C(=C(\[H])/[C@]4([H])CC[C@]([H])([C@@]([H])(C4)OC)O)/C)[C@]([H])(C)[C@]([H])(CC1=O)O)(O)O2)OC)OC

InChI

InChIKey=ZDQSOHOQTUFQEM-NURRSENYSA-N
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

HIDE SMILES / InChI

Molecular Formula C43H69NO12
Molecular Weight 792.0091
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 14
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10794694 | https://www.ncbi.nlm.nih.gov/pubmed/23957229 | https://www.ncbi.nlm.nih.gov/pubmed/10197049 | https://www.ncbi.nlm.nih.gov/pubmed/26794830 | https://www.ncbi.nlm.nih.gov/pubmed/24628911

Immunomycin (Ascomycin, FR-900520, FK520) is a macrocyclic lactone produced by S. hygroscopicus. It is well known as an antifungal and antibiotic agent. Immunomycin is an analog of FK506 and also contains a 23-membered ring. Both FK506 and Immunomycin bind to FKBP12 at the same binding site for hindering calcineurin. Thus, Immunomycin possesses immunosuppressive activity similar to that of FK506. It appears that Immunomycin inhibits the production of Th1 (interferon- and IL-2) and Th2 (IL-4 and IL-10) cytokines. Additionally, Immunomycin preferentially inhibits the activation of mast cells, an important cellular component of the atopic response. Immunomycin produces a more selective immunomodulatory effect in that it inhibits the elicitation phase of allergic contact dermatitis but does not impair the primary immune response when administered systemically. Immunomycin is a member of the polyketide group of compounds. The polyketide synthase (PKS) enzyme is used to produce polyketides. The preparation of polyketide compounds has low product yield with traditional chemical methodology using wild-type cells. Reeves et al. provide a novel method of preparing a polyketide using a host cell with a recombinant DNA vector. The recombinant DNA vector contains nucleic acids that can encode the Immunomycin PKS enzyme. Immunomycin synthesized using this technology yields PKS at higher levels than that achieved by PKS in nature.

Originator

Sources: J. Antibiotics (Tokyo) (1962), 15, (Ser. A), 231-2.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 µM [IC50]
2.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Rapamycin-FKBP12 blocks proliferation, induces differentiation, and inhibits cdc2 kinase activity in a myogenic cell line.
1993 Dec 5
Tau phosphorylation in brain slices: pharmacological evidence for convergent effects of protein phosphatases on tau and mitogen-activated protein kinase.
1995 Apr
Rapamycin-FKBP inhibits cell cycle regulators of proliferation in vascular smooth muscle cells.
1995 Mar
Nephrotoxicity studies of the immunosuppressants tacrolimus (FK506) and ascomycin in rat models.
1998 Feb 6
Potent immunosuppressive C32-O-arylethyl ether derivatives of ascomycin with reduced toxicity.
1999 Jul 19
Anticonvulsant effect of the calcineurin inhibitor ascomycin on seizures induced by picrotoxin microperfusion in the rat hippocampus.
2006 Jul
Patents

Patents

Sample Use Guides

Rats were dosed intraperitoneally once a day for 14 consecutive days with Ascomycin (1.5, 5, 15, 50 mg/kg/day).
Route of Administration: Intraperitoneal
The cytotoxic effect of FK520 on S. cerevisiae control cells (AD1–8u-) and on cells over-expressing Cdr1 protein (AD-CDR1), Pdr5 protein (AD-PDR5), and Mdr1 protein (AD-MDR1) was determined by growth inhibition assay. Yeast cells (104) were seeded into 96-well plates in the absence and the presence of varying concentrations of FK520 (1–200 mkg/mL) and were grown for 48 h at 30 °C. Absorbance was measured using a microplate spectrophotometer at 600 nm. The percentage of growth inhibition was calculated considering the growth of cells without the inhibitor as 100% as (mean absorbance in test wells)/(mean absorbance in control wells) x 100.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:38:24 UTC 2021
Edited
by admin
on Fri Jun 25 21:38:24 UTC 2021
Record UNII
AUF4U5NSJK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASCOMYCIN
Common Name English
FR-900520
Code English
IMMUNOMYCIN
Common Name English
FK-520
Code English
TACROLIMUS RELATED COMPOUND A [USP-RS]
Common Name English
CHANGCHUANMYCIN
Common Name English
FR-520
Code English
NSC-106410
Code English
L-683590
Code English
TACROLIMUS RELATED COMPOUND A [USP]
Common Name English
TACROLIMUS IMPURITY, ASCOMYCIN- [USP]
Common Name English
TACROLIMUS RELATED COMPOUND A
USP  
Common Name English
TACROLIMUS MONOHYDRATE IMPURITY A [EP]
Common Name English
TACROLIMUS RELATED COMPOUND A RS [USP]
Common Name English
Code System Code Type Description
CAS
104987-12-4
Created by admin on Fri Jun 25 21:38:24 UTC 2021 , Edited by admin on Fri Jun 25 21:38:24 UTC 2021
PRIMARY
USP_CATALOG
1642813
Created by admin on Fri Jun 25 21:38:24 UTC 2021 , Edited by admin on Fri Jun 25 21:38:24 UTC 2021
PRIMARY USP-RS
FDA UNII
AUF4U5NSJK
Created by admin on Fri Jun 25 21:38:24 UTC 2021 , Edited by admin on Fri Jun 25 21:38:24 UTC 2021
PRIMARY
MESH
C058028
Created by admin on Fri Jun 25 21:38:24 UTC 2021 , Edited by admin on Fri Jun 25 21:38:24 UTC 2021
PRIMARY
CAS
135635-46-0
Created by admin on Fri Jun 25 21:38:24 UTC 2021 , Edited by admin on Fri Jun 25 21:38:24 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
PUBCHEM
5282071
Created by admin on Fri Jun 25 21:38:24 UTC 2021 , Edited by admin on Fri Jun 25 21:38:24 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP