HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Phenoxymethylpenicillin
phenoxymethylpenicillin · v-cillin · (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid · ospen · pen-v · v-cil · apopen · acipenv
Identifikatoren & physikalische Daten
| CAS No. | 87-08-1 |
|---|---|
| Summenformel | C16H18N2O5S |
| Durchschnittliche Molmasse | 350,4 g/mol |
| Monoisotopische Masse | 350,09364268 g/mol |
| SMILES | CC1(C)S[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N2[C@H]1C(=O)O |
| InChIKey | BPLBGHOLXOTWMN-MBNYWOFBSA-N |
| PubChem CID | 6869 |
| ChEMBL | CHEMBL615 |
| ChEBI | CHEBI:27446 |
| EC No. | 201-722-0 |
| DTXSID | DTXSID3023429 |
| Lokaler Name | Phenoxymethylpenicillin |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 121 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 24 |
| Formalladung | 0 |
| Komplexität | 547 |
| Arzneimittel | Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland |
| pH | 2.5-4.0 (saturated solution) |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | 1.41.95 |
| Geruch | Odorless |
| Color/Form | white, crystalline powder |
| Löslichkeit | less than 1 mg/mL at 55 °F (NTP, 1992)<0.1 g/100mLIn water at pH 1.8 (acidified with hydrochloric acid)= 24 mg/100 mlsoluble in polar organic solventspractically insol in vegetable oils and in liquid petrolatum.Sol in alcohol and acetoneinsoluble in fixed oils4.54e-01 g/LVery slightly soluble in water, soluble in ethanol (96 per cent). |
| Human Drugs | Breast FeedingLactationAnti-Infective AgentsAntibacterial AgentsPenicillinsFDA approved drugs -> Active ingredientAccess group antibiotics |
| Schmelzpunkt | 248 to 262 °F (Decomposes) (NTP, 1992)120 - 128 °C120-1280C (dec) |
| Optical Rotation | The biologically active form is the dextrorotatory D-formthe DL-form is half as active. L-Penicillin V has little, if any, antibiotic activity. Maximum absorption: 268, 274 nm (E= 1330, 1100). |
| Physical Description | Penicillin v is a white crystalline powder. (NTP, 1992)Solid |
| Stability/Shelf Life | Stable in air up to 37 °Crelatively stable to acid.Following reconstitution, penicillin V potassium oral soln should be refrigerated @ 2-8 °C, and any unused soln should be discarded after 14 days. /Penicillin V potassium/Penicillins are generally inactivated in the presence of heat, alkaline or acid pH, oxidizing agents, alcohols, glycols, and metal ions such as copper, mercury, or zinc. In currently available penicillins, cleavage at any point in the penicillin nucleus, including the beta-lactam ring, results in complete loss of antibacterial activity. The major cause of inactivation of penicillins is hydrolysis of the beta-lactam ring. The course of hydrolysis and nature of the degradation products can vary and are generally influenced by pH. /Penicillins/In the dry state, natural penicillins and their salts are generally stable for several yr @ room temphowever, the drugs deteriorate more rapidly @ higher temp. /Natural penicillins/Solutions of penicillin begin to deteriorate upon standing a few days, even in the cold. /Penicillin V potassium/ |
| Siedepunkt | 681.4±55.0 °C(Predicted) |
| Dichte | 1.3121 (rough estimate) |
| Brechungsindex | 1.6510 (estimate) |
| Lagerbedingungen | −20°C |
| pKa (Säurekonstante) | 2.44±0.50(Predicted) |
| Aggregatzustand | A solid |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| EPA chemische Informationen | Penicillin V (87-08-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-, [2S-(2.alpha.,5.alpha.,6.beta.)]-: Human health tier I assessment |
| Brandgefahren | Flash point data for this chemical are not availablehowever it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include hypersensitization, skin rashes, contact dermatitis, oral lesions, fever, eosinophilia, interstitial nephritis, angioedema, serum sickness, anaphylaxis, "Arthus" phenomenonirritation of the Gastrointestinal tractphlebitisbronchoconstriction with severe asthma, or abdominal pain, nausea, vomiting, extreme weakness and fall in blood pressure, diarrhea, and purpuric skin eruptions. (NTP, 1992) |
| FDA-Anforderungen | Oral Dosage Form New Animal Drugs. Specifications and conditions of use provided for dogs and cats. /Penicillin V potassium for oral solution/Oral Dosage Form New Animal Drugs. Specifications and conditions of use provided for dogs and cats. /Penicillin V potassium tablets/Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392). |
| Reaktive Gruppe | Acids, Carboxylic |
| Reactivity Profile | Stable in air up to 37%relatively stable to acid. This compound is incompatible with acids, oxidizing agents (especially in the presence of trace metals), heavy metal ions such as copper, lead, zinc and mercuryglycerol, sympathomimetic amines, thiomersal, wood alcohols, cetostearyl alcohol, hard paraffins, macrogols, cocoa butter and many ionic an nonionic surface-active agents. It is also incompatible with alkalis, compounds leached from vulcanized rubber, hydrochlorides of tetracyclines and organic peroxides. Other incompatibilities include reducing agents, alcohols, other hydroxy compounds, self-emulsifying stearyl alcohol, emulsifying wax, lanolin, crude cholinesterated bases, glycol, sugars, amines, aminacrine hydrochloride, ephedrine, procaine, rubber tubing, thiamine hydrochloride, zinc oxide, oxidized cellulose, iodine, iodides, thiols, chlorocresol and resorcinol. It may also be incompatible with naphthalene oils and vitamin B. (NTP, 1992) |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Skin Sens. 1 (100%) |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Lagerbedingungen | Commercially available penicillin V ... tablets and powders for oral suspension or solution should be stored in tight containers at 15-30 °C. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with ethanol, and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Wechselwirkungen | Oral neomycin has been shown to decrease the absorption of penicillin V ... .Since penicillin acts by inhibiting cell wall synthesis, agents which inhibit protein synthesis (eg, chloramphenicol) could ... mask the bactericidal effect of penicillin. /Penicillin/Since penicillin acts by inhibiting cell wall synthesis, agents which inhibit protein synthesis (eg, erythromycin) could ... mask the bactericidal effect of penicillin. ... Clinical evidence exists for erythromycin-penicillin antagonism in patients with group A hemolytic streptococcal pharyngitis. ... The possibility of antagonism exists, but it has not been sufficiently documented in clinical studies. /Penicillin/Tetracyclines ... may interfere with a bactericidal agent such as penicillin. /Penicillin/For more Interactions (Complete) data for PENICILLIN V (16 total), please visit the HSDB record page. |
| Human Toxicity Excerpts | Hypersensitivity reactions are one of the most frequent adverse reactions to penicillin G & penicillin V. In addition ... oral admin ... is frequently associated with adverse GI effects.In addition to eosinophilia & hemolytic anemia ... other adverse hematologic effects including transient neutropenia, leukopenia, thrombocytopenia, & thrombocytopenic purpura have occurred rarely in patients receiving penicillin G or penicillin V. These hematologic reactions occur most frequently when high doses of penicillin G are admin IV & are generally reversible following discontinuance of the drugs. ... Some or the most frequent adverse reactions to orally admin penicillin ... V are GI effects including nausea, vomiting, epigastric distress & diarrhea.Skin rashes of all types may be caused by allergy to penicillin. Scarlatiniform, morbilliform, urticarial, vesicular, and bullous eruptions may develop. Purpuric lesions are uncommon & are usually the result of a vasculitis ... Henoch-Schoenlein purpura with renal involvement has been a rare complication. ... The most serious hypersensitivity reactions produced by the penicillins are angioedema and anaphylaxis. Angioedema with marked swelling of the lips, tongue, face, & periorbital tissues, frequently accompanied by asthmatic breathing & "giant hives" ... observed after topical, oral or systemic admin of penicillins of various types. ... Anaphylactoid reactions may occur at any age. ... About 0.002% of patients treated with these agents die from anaphylaxis. It has been estimated that there are at least 300 deaths per yr due to this complication of therapy. /Penicillins/Anaphylaxis has most often followed the injection of penicillin, although it has also been observed after oral ingestion of the drug, & has even resulted from the intradermal instillation of a very small quantity for the purpose of testing for the presence of hypersensitivity. ... The most dramatic /clinical picture/ is sudden, severe hypotension & rapid death. ... Bronchoconstriction with severe asthma, or abdominal pain, nausea, and vomiting, or extreme weakness & fall in blood pressure, or diarrhea & purpuric skin eruptions have characterized the anaphylactic episodes. Serum sickness varies from mild fever, rash, and leukopenia to severe arthralgia or arthritis, purpura, lymphadenopathy, splenomegaly, mental changes, ECG abnormalities suggestive of myocarditis, generalized edema, albuminuria, and hematuria. It is mediated by IgG antibodies. /Penicillins/For more Human Toxicity Excerpts (Complete) data for PENICILLIN V (45 total), please visit the HSDB record page. |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)penicillin vDILI NegativeOralDOI:10.1016/j.drudis.2019.09.022 |
| Probable Routes of Human Exposure | Veterinarians, physicians, nurses, and pharmacists have occasionally experienced contact dermatitis after handling penicillin preparations. |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Zollcode | 29411094 |
| RTECS-Nr. | RY4025000 |
| R-Sätze (R) | 42/43 |
| Toxizität | LD50 oral in rat: > 2220mg/kg |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 22-36 |
| Gefahrstoffdaten | 87-08-1(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Phenoxymethylpenicillin or penicillin V is acid-resistant and used instead of penicillin G for oral use. It is active with respect to Gram-positive (staphylococcus, streptococcus, pneumococcus), and Gram-negative (meningococcus, gonococcus) cocci, spirochaeta, clostridia, and corynebacteria. Phenoxymethylpenicillin is used for bronchitis, pneumonia, angina, scarlet fever, gonorrhea, syphilis, purulent skin and soft-tissue wounds, and other infectious diseases. Synonyms of this drug are bermycin, isocillin, cristapen, fenospen, uticillin, and others.