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(-)-Anisomycin

(-)-Anisomycin structure

CAS No:
22862-76-6
Formula:
C14H19NO4
Chemical Name:
(-)-Anisomycin
Synonyms:
3,4-Pyrrolidinediol,2-[(4-methoxyphenyl)methyl]-,3-acetate,(2R,3S,4S)-;3,4-Pyrrolidinediol,2-[(4-methoxyphenyl)methyl]-,3-acetate,[2R-(2α,3α,4β)]-;Anisomycin;3,4-Pyrrolidinediol,2-(p-methoxybenzyl)-,3-acetate,(2R,3S,4S)-;(2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate;(2R,3S,4S)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine;Flagecidin;(-)-Anisomycin;Anisomycin,(-)-;NSC 76712;Wuningmeisu C;2322-08-9;11023-48-6
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Anisomycin is a potent protein synthesis inhibitor which interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.

(-)-anisomycin is an antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system. It has a role as an antiparasitic agent, a DNA synthesis inhibitor, a protein synthesis inhibitor, an antineoplastic agent, an antimicrobial agent, a bacterial metabolite and an anticoronaviral agent. It is a monohydroxypyrrolidine and an organonitrogen heterocyclic antibiotic.|Anisomycin (sometimes known as flagecidin), is an antibiotic retrieved from the bacteria Streptomyces griseolus. This drug acts to inhibit bacterial protein and DNA synthesis.|An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.

Anisomycin (22862-76-6) activates JNK/SAPKs and reduces c-fos and c-jun. Protein synthesis inhibitor. Anisomycin induces apoptosis and sensitizes cells to anoikis. Cell permeable.

Crystalline

Poison by ingestion,intraperitoneal, subcutaneous, and intravenous routes.When heated to decomposition it emits toxic fumes ofNOx.

(-)-Anisomycin Basic Attributes

Molecular Weight：

265.3

Exact Mass：

265.30

BRN：

20705

EC Number：

245-269-7

UNII：

6C74YM2NGI

NSC Number：

76712

DSSTox ID：

DTXSID5040966

Color/Form：

white

HScode：

29419090

Characteristics

λmax：

283nm(EtOH)(lit.)

PSA：

67.8

XLogP3：

0.42

Appearance：

white solid

Density：

1.1356 (rough estimate)

Melting Point：

140-141 C

Boiling Point：

408.52°C (rough estimate)

Flash Point：

87℃

Refractive Index：

1.5230 (estimate)

Water Solubility：

Soluble in water at 2 mg/ml, in DMSO at 20mg/ml, and in methanol at 20mg/ml

Storage Conditions：

2-8°C

Toxicity：

LD50 orl-rat: 72 mg/kg ANTCAO 5,490,55

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxide fumes

Specific rotation：

D23 -30° (methanol)

PKA：

7.9(at 25℃)

Critical Temperature & Pressure：

Inert atmosphere,Store in freezer, under -20°C

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 3462 6.1/PG 3

wgk germany：

hazard class code：

T,Xn

safety instructions：

45-36-26

RTECS Number：

BZ9800000

Marks：

T,Xn

Storage features：

+4°C

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P301 + P310

Hazard Statements：

25-36/37/38-20/21/22

RIDADR：

UN 3462 6.1/PG 3

GHS Classification：

|Danger|H301 (98.41%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 63 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

highly toxic

Drug Information

MeSH：

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)|Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

MeSH Entry Terms：

Anisomycin

(-)-Anisomycin Use and Manufacturing

Anisomycin is a phenylmethylenepyrrolidine first isolated from Streptomyces griseolus in 1954 as an antiprotozoan with antifungal activity. Anisomycin is an inhibitor of protein synthesis by binding to the 60S ribosomal subunit. Interestingly, anisomycin has found use for the induction of amnesia in animal models. More recently, anisomycin has been demonstrated to induce apoptosis, to be a selective signalling agonist, to activate mitogen-activated protein (MAP) kinases and to be immunomodulatory via its action on T cells.

It is applied as an antiparasitic agent and antineoplastic agent. It acts as a protein synthesis inhibitor (blocks translation), potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. It also scts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK).

Computed Properties

Molecular Weight:265.30
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:265.13140809
Monoisotopic Mass:265.13140809
Topological Polar Surface Area:67.8
Heavy Atom Count:19
Complexity:302
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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