Plerixafor

Identification

Summary

Plerixafor is a CXCR4 antagonist used in combination with granulocyte-colony stimulating factor to mobilize hematopoietic stem cells to the peripheral blood for collection and autologous transplantation in patients with non-Hodgkin’s lymphoma and multiple myeloma.

Brand Names
Mozobil
Generic Name
Plerixafor
DrugBank Accession Number
DB06809
Background

Plerixafor is a small-molecule inhibitor of C-X-C chemokine receptor type 4 (CXCR4) that acts as a hematopoietic stem cell mobilizer.5,9 It is used to stimulate the release of stem cells from the bone marrow into the blood in patients with non-Hodgkin's lymphoma (NHL) and multiple myeloma to stimulate their immune system. These stem cells are then collected and used in autologous stem cell transplantation to replace blood-forming cells destroyed by chemotherapy.6,9

As an inhibitor of CXCR4, plerixafor blocks the binding of its ligand, stromal cell-derived factor-1-alpha (SDF-1α). Since CXCR4 and SDF-1α are involved in the trafficking and homing of CD34+ cells to the marrow compartment, blocking this interaction leads to an increase in CD34+ cell circulating levels.5 Compared to placebo with G-CSF, the plerixafor and G-CSF mobilization regimen has a higher probability of achieving the optimal CD34+ cell target for tandem transplantation in fewer apheresis procedures.3

Plerixafor has orphan drug status in the United States and European Union and was approved by the US Food and Drug Administration on December 15, 2008.5,9

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 502.782
Monoisotopic: 502.447143768
Chemical Formula
C28H54N8
Synonyms
  • 1,1'-(1,4-phenylenebis(methylene))bis-1,4,8,11-tetraazacyclotetradecane
  • 1,4,8,11-tetraazacyclotetradecane, 1,1'-(1,4-phenylenebis(methylene))bis-
  • Plerixafor

Pharmacology

Indication

Plerixafor is indicated in combination with granulocyte-colony stimulating factor (G-CSF) to mobilize hematopoietic stem cells (HSCs) to the peripheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin’s lymphoma or multiple myeloma.9

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Plerixafor is a bicyclam derivative that antagonizes C-X-C chemokine receptor type 4 (CXCR4) by binding to three acidic residues in the ligand-binding pocket: Asp171, Asp262, and Glu288.7,10 Blood levels of CD34+ cells peaked between 6 and 9 hours after the administration of 0.24 mg/kg plerixafor in healthy subjects. In combination with a granulocyte-colony stimulating factor (G-CSF), circulating CD34+ cells in the peripheral blood peaked between 10 and 14 hours. The use of plerixafor is not associated with QT/QTc prolongation at single doses up to 0.40 mg/kg.9

Serious hypersensitivity reactions, such as anaphylactic-type reactions, have occurred in patients receiving plerixafor. The use of plerixafor may also cause tumor cell mobilization in leukemia patients, splenic enlargement and rupture, embryo-fetal toxicity, and hematologic effects, such as leukocytosis and thrombocytopenia. When used in combination with G-CSF for hematopoietic stem cell mobilization‚ plerixafor may lead to the release of tumor cells from the marrow and their subsequent collection in the leukapheresis product.9

Mechanism of action

Plerixafor inhibits the C-X-C chemokine receptor type 4 (CXCR4) on CD34+ cells and reversibly blocks the binding of its ligand, stromal cell-derived factor-1-alpha (SDF-1α). SDF-1α and CXCR4 play a role in the trafficking and homing of human hematopoietic stem cells (HSCs) to the marrow compartment. In the marrow, stem cell CXCR4 can help anchor HSCs to the marrow matrix, either directly via SDF-1α or through the induction of other adhesion molecules. By blocking the interaction between SDF-1α and CXCR4 with plerixafor, the mobilization of progenitor cells is triggered. Adding granulocyte-colony stimulating factor (G-CSF) to enhance CD34+ cell mobilization increases the yield of stem cells, an important determinant of graft adequacy.1,2,9

TargetActionsOrganism
AC-X-C chemokine receptor type 4
antagonist
inhibitor
Humans
Absorption

Plerixafor follows a two-compartment pharmacokinetic profile with first-order absorption and exhibits linear kinetics between 0.04 mg/kg and 0.24 mg/kg. The pharmacokinetic profile of plerixafor in healthy subjects was similar to the one observed in patients with non-Hodgkin’s lymphoma (NHL) and multiple myeloma (MM) who received plerixafor in combination with granulocyte-colony stimulating factor (G-CSF). In addition, the clearance of plerixafor has a significant relationship with creatinine clearance (CLCR). The population pharmacokinetic analysis showed that, with increasing body weight, a mg/kg-based dosage leads to a higher plerixafor exposure (AUC0-24h). However, NHL patients (<70 kg) given a fixed dose of 20 mg of plerixafor had an AUC0-10h 1.43-fold higher than the one detected in patients given 0.24 mg/kg of plerixafor. Therefore, a body weight of 83 kg was selected as an appropriate cut-off point to transition patients from fixed to weight-based dosing.9

Peak concentrations are reached in approximately 30-60 minutes (tmax) following subcutaneous injection.9,10 In patients given 0.24 mg/kg of plerixafor subcutaneously after receiving 4-days of G-CSF pre-treatment, the Cmax and AUC0-24 were 887 ng/ml and 4337 ng·hr/ml, respectively.10

Volume of distribution

Plerixafor has an apparent volume of distribution of 0.3 L/kg.9

Protein binding

The human plasma protein binding of plerixafor is up to 58%.9

Metabolism

Plerixafor is not metabolized by the liver and is not a metabolism-dependent inhibitor of major cytochrome P450 enzymes, including 1A2, 2C9, 2C19, 2D6 and 3A4. In addition, it does not induce cytochrome P450 1A2, 2B6, or 3A4 enzymes.9 Plerixafor is metabolically stable, and in vivo studies in rats and dogs showed that the non-parent radiolabelled components in plasma and urine were Cu2+ complexes with plerixafor. This is consistent with the presence of two cyclam rings in plerixafor, which may act as potential chelating sites.13

Route of elimination

Plerixafor is mainly eliminated through urine. In healthy volunteers with normal renal function given 0.24 mg/kg of plerixafor, approximately 70% of the parent drug is excreted in urine in the first 24 hours. An in vitro study with MDCKII and MDCKII-MDR1 cell models found that plerixafor is not a substrate or inhibitor of P-glycoprotein.9

Half-life

Plerixafor has a distribution half-life of 0.3 hours and a terminal population half-life of 5.3 hours in patients with normal renal function. In studies with healthy subjects and patients, the terminal half-life in plasma ranges between 3 and 5 hours.9 In patients with non-Hodgkin lymphoma, the terminal half-life of plerixafor is 4.4 hours, and in patients with multiple myeloma, the terminal half-life is 5.6 hours.4

Clearance

Plerixafor has a total plasma clearance of 4.38 L/h, and a renal clearance of 3.15 L/h.4,8

Adverse Effects
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Toxicity

There is limited data about the effects of plerixafor at doses higher than the recommended (0.24 mg/kg subcutaneously). However, the frequency of gastrointestinal disorders, vasovagal reactions, orthostatic hypotension, and/or syncope may be higher.9 The carcinogenicity of plerixafor has not been evaluated, and the effect of plerixafor on human fertility is unknown. According to the results from an in vitro bacterial mutation assay, an in vitro chromosomal aberration test, and an in vivo bone marrow micronucleus test in rats after subcutaneous doses up to 25 mg/kg, plerixafor is not genotoxic.9 In mice and rats, the LD50 of plerixafor by intravenous injection is 5 mg/kg. The LD50 of plerixafor by subcutaneous injection is 16 mg/kg in mice and >50 mg/kg in rats/.11

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Plerixafor which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Plerixafor which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Plerixafor which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Plerixafor which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Plerixafor which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Plerixafor octahydrochlorideOD49913540155148-31-5UEUPDYPUTTUXLJ-UHFFFAOYSA-N
International/Other Brands
Mozobil (Genzyme Corporation)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MozobilSolution20 mg / mLSubcutaneousSanofi Aventis2012-03-26Not applicableCanada flag
MozobilInjection, solution20 mg/mlSubcutaneousSanofi B.V.2020-12-23Not applicableEU flag
MozobilInjection, solution24 mg/1.2mLSubcutaneoussanofi-aventis U.S. LLC2013-09-01Not applicableUS flag
MozobilSolution24 mg/1.2mLSubcutaneousGenzyme Corporation2008-12-152018-03-23US flag
Plerixafor AccordInjection, solution20 mg/mlSubcutaneousAccord Healthcare S.L.U.2023-02-08Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PlerixaforSolution24 mg/1.2mLSubcutaneousMeitheal Pharmaceuticals Inc.2023-07-24Not applicableUS flag
PlerixaforInjection, solution24 mg/1.2mLSubcutaneousGland Pharma Limited2024-05-03Not applicableUS flag
PlerixaforInjection24 mg/1.2mLSubcutaneousZydus Lifesciences Limited2023-07-28Not applicableUS flag
PlerixaforInjection, solution24 mg/1.2mLSubcutaneousNovadoz Pharmaceuticals Llc2023-07-25Not applicableUS flag
PlerixaforSolution24 mg/1.2mLSubcutaneousDr. Reddy's Laboratories Inc2023-11-06Not applicableUS flag

Categories

ATC Codes
L03AX16 — Plerixafor
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylmethylamines
Alternative Parents
Benzylamines / Aralkylamines / Trialkylamines / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzylamine / Hydrocarbon derivative / Organic nitrogen compound / Organoheterocyclic compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
S915P5499N
CAS number
110078-46-1
InChI Key
YIQPUIGJQJDJOS-UHFFFAOYSA-N
InChI
InChI=1S/C28H54N8/c1-9-29-15-17-31-13-3-21-35(23-19-33-11-1)25-27-5-7-28(8-6-27)26-36-22-4-14-32-18-16-30-10-2-12-34-20-24-36/h5-8,29-34H,1-4,9-26H2
IUPAC Name
1-({4-[(1,4,8,11-tetraazacyclotetradecan-1-yl)methyl]phenyl}methyl)-1,4,8,11-tetraazacyclotetradecane
SMILES
C(N1CCCNCCNCCCNCC1)C1=CC=C(CN2CCCNCCNCCCNCC2)C=C1

References

Synthesis Reference

Xu, D., et al. (1997). Process for preparing 1,1'-[1,4-phenylenebis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane (U.S. Patent No. 5,612,478 A). U.S. Patent and Trademark Office. https://patentimages.storage.googleapis.com/23/2a/c4/cdec2e80dbe460/US5612478.pdf

General References
  1. Uy GL, Rettig MP, Cashen AF: Plerixafor, a CXCR4 antagonist for the mobilization of hematopoietic stem cells. Expert Opin Biol Ther. 2008 Nov;8(11):1797-804. doi: 10.1517/14712598.8.11.1797 . [Article]
  2. Fricker SP: A novel CXCR4 antagonist for hematopoietic stem cell mobilization. Expert Opin Investig Drugs. 2008 Nov;17(11):1749-60. doi: 10.1517/13543784.17.11.1749 . [Article]
  3. DiPersio JF, Stadtmauer EA, Nademanee A, Micallef IN, Stiff PJ, Kaufman JL, Maziarz RT, Hosing C, Fruehauf S, Horwitz M, Cooper D, Bridger G, Calandra G: Plerixafor and G-CSF versus placebo and G-CSF to mobilize hematopoietic stem cells for autologous stem cell transplantation in patients with multiple myeloma. Blood. 2009 Jun 4;113(23):5720-6. doi: 10.1182/blood-2008-08-174946. Epub 2009 Apr 10. [Article]
  4. Stewart DA, Smith C, MacFarland R, Calandra G: Pharmacokinetics and pharmacodynamics of plerixafor in patients with non-Hodgkin lymphoma and multiple myeloma. Biol Blood Marrow Transplant. 2009 Jan;15(1):39-46. doi: 10.1016/j.bbmt.2008.10.018. [Article]
  5. Brave M, Farrell A, Ching Lin S, Ocheltree T, Pope Miksinski S, Lee SL, Saber H, Fourie J, Tornoe C, Booth B, Yuan W, He K, Justice R, Pazdur R: FDA review summary: Mozobil in combination with granulocyte colony-stimulating factor to mobilize hematopoietic stem cells to the peripheral blood for collection and subsequent autologous transplantation. Oncology. 2010;78(3-4):282-8. doi: 10.1159/000315736. Epub 2010 Jun 8. [Article]
  6. Choi HY, Yong CS, Yoo BK: Plerixafor for stem cell mobilization in patients with non-Hodgkin's lymphoma and multiple myeloma. Ann Pharmacother. 2010 Jan;44(1):117-26. doi: 10.1345/aph.1M380. Epub 2009 Dec 15. [Article]
  7. Keating GM: Plerixafor: a review of its use in stem-cell mobilization in patients with lymphoma or multiple myeloma. Drugs. 2011 Aug 20;71(12):1623-47. doi: 10.2165/11206040-000000000-00000. [Article]
  8. MacFarland R, Hard ML, Scarborough R, Badel K, Calandra G: A pharmacokinetic study of plerixafor in subjects with varying degrees of renal impairment. Biol Blood Marrow Transplant. 2010 Jan;16(1):95-101. doi: 10.1016/j.bbmt.2009.09.003. Epub 2009 Sep 10. [Article]
  9. FDA Approved Drug Products: MOZOBIL (plerixafor) injection for subcutaneous use (August 2020) [Link]
  10. EMA Summary of Product Characteristics: Mozobil (plerixafor) injection solution for subcutaneous use (April 2014) [Link]
  11. FDA Pharmacology Review: Mozobil (plerixafor) injection (December 2008) [Link]
  12. Toronto Research Chemicals: Plerixafor SDS [Link]
  13. CHMP Assessment Report: Mozobil (plerixafor) [Link]
Human Metabolome Database
HMDB0015681
KEGG Drug
D08971
PubChem Compound
65015
PubChem Substance
99443297
ChemSpider
58531
BindingDB
50035696
RxNav
733003
ChEBI
125354
ChEMBL
CHEMBL18442
ZINC
ZINC000022443609
PharmGKB
PA165958410
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
VH6
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Plerixafor
PDB Entries
8u4p

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4CompletedTreatmentAutologous hematopoietic stem cell transplant1somestatusstop reasonjust information to hide
4CompletedTreatmentDiabetes1somestatusstop reasonjust information to hide
4CompletedTreatmentNon-Hodgkin's Lymphoma (NHL)1somestatusstop reasonjust information to hide
4RecruitingTreatmentLymphoma1somestatusstop reasonjust information to hide
4Unknown StatusTreatmentAutologous Stem Cell Transplantation1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionParenteral; Subcutaneous20 MG/ML
Injection, solutionSubcutaneous24 mg/1.2mL
SolutionSubcutaneous20 mg / mL
SolutionSubcutaneous24 mg/1.2mL
SolutionSubcutaneous24.000 mg
SolutionSubcutaneous20 mg/ml
Injection, solutionSubcutaneous20 mg/ml
SolutionSubcutaneous24 mg
InjectionSubcutaneous24 mg/1.2mL
Injection, solution20 MG/ML
Injection, solutionParenteral20 mg/ml
Injection, solution20 mg/1ml
SolutionSubcutaneous20 mg/1ml
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6987102No2006-01-172023-07-22US flag
US7897590No2011-03-012023-03-22US flag
USRE42152No2011-02-152018-12-10US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)131.5 °CFDA label
water solubilitySlightly solubleSDS
pKa8.5-11.5 and <2.4CHMP Assessment Report
Predicted Properties
PropertyValueSource
Water Solubility0.0472 mg/mLALOGPS
logP0.62ALOGPS
logP-0.43Chemaxon
logS-4ALOGPS
pKa (Strongest Basic)10.23Chemaxon
Physiological Charge4Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area78.66 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity155.01 m3·mol-1Chemaxon
Polarizability60.65 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.932
Blood Brain Barrier+0.6867
Caco-2 permeable-0.5403
P-glycoprotein substrateSubstrate0.8076
P-glycoprotein inhibitor INon-inhibitor0.8119
P-glycoprotein inhibitor IINon-inhibitor0.7683
Renal organic cation transporterInhibitor0.5069
CYP450 2C9 substrateNon-substrate0.8905
CYP450 2D6 substrateSubstrate0.5274
CYP450 3A4 substrateNon-substrate0.7818
CYP450 1A2 substrateNon-inhibitor0.8787
CYP450 2C9 inhibitorNon-inhibitor0.9272
CYP450 2D6 inhibitorNon-inhibitor0.7149
CYP450 2C19 inhibitorNon-inhibitor0.9114
CYP450 3A4 inhibitorNon-inhibitor0.8817
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.926
Ames testNon AMES toxic0.7906
CarcinogenicityNon-carcinogens0.9106
BiodegradationNot ready biodegradable0.9824
Rat acute toxicity2.1178 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Inhibitor0.6334
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0udi-1697050000-f5d2d801403d4ca1fac2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0000090000-f6127c0396058e17120f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0000090000-cfb57137af8c69fff8eb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0000090000-0c686db0669edc9df7bd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-11os-0980010000-20b211b430b392a9ffaa
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0300090000-ddc0d9ecb8fc4f3b0abd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900200000-7c6ca6e9ee557f9dc70c
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-240.8298557
predicted
DarkChem Lite v0.1.0
[M-H]-213.80109
predicted
DeepCCS 1.0 (2019)
[M+H]+241.3926557
predicted
DarkChem Lite v0.1.0
[M+H]+216.34264
predicted
DeepCCS 1.0 (2019)
[M+Na]+240.4912557
predicted
DarkChem Lite v0.1.0
[M+Na]+223.19568
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Virus receptor activity
Specific Function
Receptor for the C-X-C chemokine CXCL12/SDF-1 that transduces a signal by increasing intracellular calcium ion levels and enhancing MAPK1/MAPK3 activation. Acts as a receptor for extracellular ubiq...
Gene Name
CXCR4
Uniprot ID
P61073
Uniprot Name
C-X-C chemokine receptor type 4
Molecular Weight
39745.055 Da
References
  1. Uy GL, Rettig MP, Cashen AF: Plerixafor, a CXCR4 antagonist for the mobilization of hematopoietic stem cells. Expert Opin Biol Ther. 2008 Nov;8(11):1797-804. doi: 10.1517/14712598.8.11.1797 . [Article]
  2. Jujo K, Ii M, Sekiguchi H, Klyachko E, Misener S, Tanaka T, Tongers J, Roncalli J, Renault MA, Thorne T, Ito A, Clarke T, Kamide C, Tsurumi Y, Hagiwara N, Qin G, Asahi M, Losordo DW: CXC-chemokine receptor 4 antagonist AMD3100 promotes cardiac functional recovery after ischemia/reperfusion injury via endothelial nitric oxide synthase-dependent mechanism. Circulation. 2013 Jan 1;127(1):63-73. doi: 10.1161/CIRCULATIONAHA.112.099242. Epub 2012 Nov 30. [Article]
  3. Pan C, Liu P, Ma D, Zhang S, Ni M, Fang Q, Wang J: Bone marrow mesenchymal stem cells in microenvironment transform into cancer-associated fibroblasts to promote the progression of B-cell acute lymphoblastic leukemia. Biomed Pharmacother. 2020 Oct;130:110610. doi: 10.1016/j.biopha.2020.110610. Epub 2020 Aug 12. [Article]
  4. FDA Approved Drug Products: MOZOBIL (plerixafor) injection for subcutaneous use (August 2020) [Link]

Drug created at September 14, 2010 16:21 / Updated at April 23, 2024 11:38