Pamidronic Acid

HCID 4674CAS 40391-99-9

Grundinformationen

Standard-SMILES
NCCC(O)(P(=O)(O)O)P(=O)(O)O
InChIKey
WRUUGTRCQOWXEG-UHFFFAOYSA-N
Summenformel
C3H11NO7P2
Durchschnittliche Molmasse
235,07 g/mol
Monoisotopische Masse
235,00107495

Überblick

Pamidronate is a phosphonoacetic acid.

Namen und Bezeichner

Bevorzugter Name
Pamidronic Acid
IUPAC
(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid

Namen und Synonyme

PAMIDRONIC ACIDpamidronate40391-99-9AmidronateAcide pamidronique(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acidAcido pamidronicoAcidum pamidronicumRibodroat(3-Amino-1-hydroxypropylidene)bisphosphonic acidDTXSID4023414AHPrBP
Weitere Namen anzeigen
OYY3447OMC(3-Amino-1-hydroxypropylidene)diphosphonic acidDTXCID003414(3-amino-1-hydroxypropylidene)-1,1-biphosphonateaminopropanehydroxydiphosphonateamino-1-hydroxypropane-1,1-diphosphonateRefChem:57113M05BA03

Datenbank-Bezeichner

CAS
40391-99-9
PubChem CID
4674
DTXSID
DTXSID4023414
ChEMBL
CHEMBL834
ChEBI
CHEBI:7903
UNII
OYY3447OMC
EC Number
254-905-2
Nikkaji
J221.669H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-6,9
Polarare Oberfläche (TPSA)
161 Ų
H-Brücken-Donoren
6
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
4
Schwere Atome
13

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

LogP-4.7
Solubility1.58e+01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Bisphosphonates; Bone Density Conservation Agents; Diphosphonates
Melting Point254-262
Physical DescriptionSolid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 24 reports by companies from 4 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxikologische Informationen

TreatmentIf overdosage occurs, symptomatic hypocalcemia could also result; such patients should be treated with short-term intravenous calcium. (L1712)
Health EffectsRare cases of uveitis, iritis, scleritis, and episcleritis have been reported, including one case of scleritis, and one case of uveitis upon separate rechallenges.
Adverse EffectsPamidronate correlates with numerous adverse effects, including hypocalcemia and resulting secondary hyperparathyroidism, acute phase response, musculoskeletal pain, various ocular events, and osteonecrosis of the jaw.
Exposure RoutesParenteral (intravenous). Plasma concentration rises rapidly upon IV administration.
Toxicity Summary · 2 Einträge

A small number of cases describe symptomatic hypocalcemia following pamidronate administration. In each case, however, patients had pre-existing derangements contributing to their symptoms, including renal insufficiency and low vitamin D levels secondary to lifestyle, previous GI surgery, and medication history. Recommendations for the management of pamidronate overdose include appropriate correction of the electrolyte disturbance and pre-treatment supplementation with calcium and Vitamin D.

The mechanism of action of pamidronate is inhibition of bone resorption. Pamidronate adsorbs to calcium phosphate (hydroxyapatite) crystals in bone and may directly block dissolution of this mineral component of bone. In vitro studies also suggest that inhibition of osteoclast activity contributes to inhibition of bone resorption. Pamidronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates (such as pamidronate, alendronate, risedronate, ibandronate and zoledronate) appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting 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 SymptomsSide effects include an allergic reaction, kidney problems, seizures, low levels of calcium, magnesium, or phosphorus in the blood

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

M05BA03

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein BindingPamidronate is approximately 54% protein bound in serum.
Pharmacodynamics · 1 Eintrag

Pamidronic acid is a second generation, nitrogen containing bisphosphonate that inhibits osteoclast mediated bone loss It has a wide therapeutic index and a long duration of action as it can be given every 3-4 weeks for certain indications. Patients should be counselled regarding the risk of elevated blood urea nitrogen, renal tubular necrosis, and nephrotoxicity.

Mechanism of Action · 1 Eintrag

Bisphosphonates are taken into the bone where they bind to hydroxyapatite. Bone resorption by osteoclasts causes local acidification, releasing the bisphosphonate, which is taken into the osteoclast by fluid-phase endocytosis. Endocytic vesicles become acidified, releasing bisphosphonates into the cytosol of osteoclasts where they act. Osteoclasts mediate resorption of bone. When osteoclasts bind to bone they form podosomes, ring structures of F-actin. Disruption of the podosomes causes osteoclasts to detach from bones, preventing bone resorption. Nitrogen containing bisphosphonates such as pamidronate are known to induce apoptosis of hematopoietic tumor cells by inhibiting the components of the mevalonate pathway farnesyl diphosphate synthase, farnesyl diphosphate, and geranylgeranyl diphosphate. These components are essential for post-translational prenylation of GTP-binding proteins like Rap1. The lack of prenylation of these proteins interferes with their function, and in the case of Rap1, leads to apoptosis. pamidronate also activated caspases 3 and 9 which further contribute to apoptosis.

Biological Half-LifeThe mean elimination half life of pamidronate is 28±7 hours.
Metabolism/Metabolites · 2 Einträge

Pamidronate is not metabolized _in vivo_.

Pamidronate is not metabolized and is exclusively eliminated by renal excretion. Route of Elimination: Pamidronate is not metabolized and is exclusively eliminated by renal excretion. Half Life: The mean ± SD elimination half-life is 28 ± 7 hours

Verwendung und Herstellung

Uses · 2 Einträge

Use (kg; approx.) in Germany (2009): >10

Pamidronate is in a class of drugs called bisphosphonates. Pamidronate reduces breakdown of the bones. Pamidronate is used in the treatment of Paget's disease of bone; to reduce high levels of calcium in the blood associated with malignancy (cancer); and to reduce the breakdown of bone due to metastases of breast cancer or multiple myeloma. For the treatment of moderate or severe hypercalcemia associated with malignancy

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