HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Ibandronate
Ibandronic · BPH 24 · Ibadronic Acid · Ibandronic acid · Ibandronate Acid · IBANDRONIC ACID-D3 · Tirofiban Impurity 67 · Ibandronic acid USP/EP/BP
Identifikatoren & physikalische Daten
| CAS No. | 114084-78-5 |
|---|---|
| Summenformel | C9H23NO7P2 |
| Durchschnittliche Molmasse | 319,23 g/mol |
| Monoisotopische Masse | 319,09497534 g/mol |
| SMILES | CCCCCN(C)CCC(O)(P(=O)(O)O)P(=O)(O)O |
| InChIKey | MPBVHIBUJCELCL-UHFFFAOYSA-N |
| PubChem CID | 60852 |
| ChEMBL | CHEMBL997 |
| EC No. | 688-095-0 |
| DTXSID | DTXSID5048340 |
Chemische & physikalische Eigenschaften
| XLogP | -4,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 139 |
| H-Brücken-Donoren | 5 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 9 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 342 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | -2.1 |
| Löslichkeit | Freely soluble1.34e+01 g/LAqueous Base (Slightly), Methanol (Slightly), Water (Slightly) |
| Human Drugs | Breast FeedingLactationBisphosphonatesBone Density Conservation AgentsDiphosphonatesEMA approved medicines: Human medicine |
| Schmelzpunkt | 113-115113-115°C |
| Physical Description | Solid |
| Collision Cross Section | 165.52 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 587.8±60.0 °C(Predicted) |
| Dichte | 1.449±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Sealed in dry,Store in freezer, under -20°C |
| pKa (Säurekonstante) | 1.60±0.10(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to Off-White |
| Stabilität | Hygroscopic |
| InChI | InChI=1S/C9H23NO7P2/c1-3-4-5-7-10(2)8-6-9(11,18(12,13)14)19(15,16)17/h11H,3-8H2,1-2H3,(H2,12,13,14)(H2,15,16,17) |
| InChIKey | MPBVHIBUJCELCL-UHFFFAOYSA-N |
| SMILES | C(P(=O)(O)O)(P(=O)(O)O)(O)CCN(C)CCCCC |
| CAS Datenbank | 114084-78-5(CAS DataBase Reference) |
| EPA chemische Informationen | Phosphonic acid, P,P'-[1-hydroxy-3-(methylpentylamino)propylidene]bis- (114084-78-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (95.2%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 21 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (95.2%) |
| Expositionspfade | Poorly absorbed (mean bioavailability following a 2.5 mg oral dose is about 0.6% compared to intravenous dosing). Absorption is impaired by any kind of food or drink other than plain water. |
| Toxizitätsübersicht | The action of ibandronate on bone tissue is based partly on its affinity for hydroxyapatite, which is part of the mineral matrix of bone. Nitrogen-containing bisphosphonates (such as pamidronate, alendronate, risedronate, ibandronate and zoledronate) appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting farnesyl pyrophosphate (FPP) synthase, an enzyme in the mevalonate pathway. Inhibition of this enzyme in osteoclasts prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are essential for the post-translational farnesylation and geranylgeranylation of small GTPase signalling proteins. This activity inhibits osteoclast activity and reduces bone resorption and turnover. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass. |
| Signs and Symptoms | LD<sub>50</sub> = 811 mg/kg (rat, oral), side effects include bronchitis, pneumonia and urinary tract infections. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)ibandronateDILI NegativeOralDOI:10.1016/j.drudis.2019.09.022 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
Anwendungen & Verwendung
Beschreibung
This third generation biphosphonate was launched in Austria and Germany for the treatment of bone disorders such as hypercalcemia in malignancy and ostedysis, Paget's disease and osteoporosis. It does not effect bone mineralization, therefore, the potential risk of osteomalacia is prevented. This was a problem with first generation derivatives. While the exact mode of action is not understood, they are inhibitors of osteroclast mediated bone resorption. These compounds strongly interact with hydroxyapatite crystals and have a half-life in the skeleton of several years. Despite this observation ibandronate was well tolerated and safe.
Verwenden
A biphosphonate bone resorption inhibitor.