Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H22N6O5.ClH |
| Molecular Weight | 390.823 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)[C@H](N)C(=O)OC[C@@H](CO)OCN1C=NC2=C1N=C(N)NC2=O
InChI
InChIKey=ZORWARFPXPVJLW-RJUBDTSPSA-N
InChI=1S/C14H22N6O5.ClH/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22;/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22);1H/t8-,9+;/m1./s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16305999http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021304s008,022257s003lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/2177317 | https://www.ncbi.nlm.nih.gov/pubmed/3265058 | https://adisinsight.springer.com/drugs/800001059http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdfCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/monograph/valganciclovir-hydrochloride.html | http://www.rxlist.com/valcyte-drug/indications-dosage.htm
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16305999http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021304s008,022257s003lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/2177317 | https://www.ncbi.nlm.nih.gov/pubmed/3265058 | https://adisinsight.springer.com/drugs/800001059http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/019661s030lbl.pdf
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/monograph/valganciclovir-hydrochloride.html | http://www.rxlist.com/valcyte-drug/indications-dosage.htm
Ganciclovir is a synthetic acyclic nucleoside analogue of 2'-deoxyguanosine active against cytomegalovirus. Ganciclovir has been shown to be active against cytomegalovirus (CMV) and herpes simplex virus (HSV) in humans. To achieve anti-CMV activity, ganciclovir is phosphorylated first to the monophosphate form by a CMV-encoded (UL97 gene) protein kinase homologue, then to the di- and triphosphate forms by cellular kinases. Ganciclovir triphosphate concentrations may be 100-fold greater in CMV-infected than in uninfected cells, indicating preferential phosphorylation in infected cells. Ganciclovir triphosphate, once formed, persists for days in the CMV-infected cell. Ganciclovir triphosphate is believed to inhibit viral DNA synthesis by (1) competitive inhibition of viral DNA polymerases; and (2) incorporation into viral DNA, resulting in eventual termination of viral DNA elongation. Ganciclovir is indicated for the treatment of CMV retinitis in immunocompromised patients, including patients with acquired immunodeficiency syndrome (AIDS) and for the treatment of acute herpetic keratitis.
Originator
Sources: https://worldwide.espacenet.com/publicationDetails/biblio?II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=19960131&CC=EP&NR=0694547A2&KC=A2http://shodhganga.inflibnet.ac.in/bitstream/10603/2450/15/15_chapter%204.pdf
Curator's Comment: The first synthesis of ganciclovir was reported by Julien Verheyden and John Martin at Syntex Research in California in 1980 and is marketed as sodium salt (Ganciclovir sodium) under the trade names Cytovene and Cymevene.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P08546 Gene ID: NA Gene Symbol: UL54 Target Organism: Human cytomegalovirus (strain AD169) (HHV-5) (Human herpesvirus 5) |
|||
| 0.08 µM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | ZIRGAN Approved UseZIRGAN is a topical ophthalmic antiviral that is indicated for the treatment of acute herpetic keratitis (dendritic ulcers). Launch Date1995 |
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| Primary | CYTOVENE Approved UseCYTOVENE-IV is indicated for the treatment of CMV retinitis in immunocompromised patients, including patients with acquired immunodeficiency syndrome (AIDS). CYTOVENE-IV is also indicated for the prevention of CMV disease in transplant recipients at risk for CMV disease. Launch Date1994 |
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| Primary | VALCYTE Approved UseVALCYTE is indicated for the treatment of CMV retinitis in patients with acquired immunodeficiency syndrome (AIDS) Launch Date2001 |
|||
| Primary | VALCYTE Approved UseVALCYTE is indicated for the prevention of CMV disease in kidney, heart, and kidney-pancreas transplant patients at high risk Launch Date2001 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.8 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10747829 |
1 g 3 times / day multiple, oral dose: 1 g route of administration: Oral experiment type: MULTIPLE co-administered: |
GANCICLOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
13.3 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16737936 |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
GANCICLOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
35.4 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10747829 |
1 g 3 times / day multiple, oral dose: 1 g route of administration: Oral experiment type: MULTIPLE co-administered: |
GANCICLOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
53.8 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16737936 |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
GANCICLOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16737936 |
5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
GANCICLOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1000 mg 6 times / day multiple, oral Highest studied dose Dose: 1000 mg, 6 times / day Route: oral Route: multiple Dose: 1000 mg, 6 times / day Sources: |
unhealthy, 37.4 n = 19 Health Status: unhealthy Condition: AIDS Age Group: 37.4 Population Size: 19 Sources: |
|
2000 mg 3 times / day multiple, oral Highest studied dose Dose: 2000 mg, 3 times / day Route: oral Route: multiple Dose: 2000 mg, 3 times / day Sources: |
unhealthy, 38.6 n = 50 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: 38.6 Population Size: 50 Sources: |
Other AEs: Neutropenia, Thrombocytopenia... Other AEs: Neutropenia (18%) Sources: Thrombocytopenia (4%) Anemia (severe, 4%) Renal impairment (4%) |
50 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 50 mg/kg, 3 times / day Route: oral Route: multiple Dose: 50 mg/kg, 3 times / day Sources: |
unhealthy, 7.4 years (range: 0.5-16.9 years) n = 36 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: 7.4 years (range: 0.5-16.9 years) Population Size: 36 Sources: |
Other AEs: Neutropenia... |
5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
Other AEs: Fever, Infection... Other AEs: Fever (48%) Sources: Infection (13%) Chills (10%) Sepsis (15%) Diarrhea (44%) Anorexia (14%) Vomiting (13%) Leukopenia (41%) Anemia (25%) Thrombocytopenia (6%) Neuropathy (9%) Sweating (12%) Pruritus (5%) Catheter infection (9%) Catheter sepsis (8%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Neutropenia | 18% | 2000 mg 3 times / day multiple, oral Highest studied dose Dose: 2000 mg, 3 times / day Route: oral Route: multiple Dose: 2000 mg, 3 times / day Sources: |
unhealthy, 38.6 n = 50 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: 38.6 Population Size: 50 Sources: |
| Renal impairment | 4% | 2000 mg 3 times / day multiple, oral Highest studied dose Dose: 2000 mg, 3 times / day Route: oral Route: multiple Dose: 2000 mg, 3 times / day Sources: |
unhealthy, 38.6 n = 50 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: 38.6 Population Size: 50 Sources: |
| Thrombocytopenia | 4% | 2000 mg 3 times / day multiple, oral Highest studied dose Dose: 2000 mg, 3 times / day Route: oral Route: multiple Dose: 2000 mg, 3 times / day Sources: |
unhealthy, 38.6 n = 50 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: 38.6 Population Size: 50 Sources: |
| Anemia | severe, 4% | 2000 mg 3 times / day multiple, oral Highest studied dose Dose: 2000 mg, 3 times / day Route: oral Route: multiple Dose: 2000 mg, 3 times / day Sources: |
unhealthy, 38.6 n = 50 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: 38.6 Population Size: 50 Sources: |
| Neutropenia | 22% | 50 mg/kg 3 times / day multiple, oral Highest studied dose Dose: 50 mg/kg, 3 times / day Route: oral Route: multiple Dose: 50 mg/kg, 3 times / day Sources: |
unhealthy, 7.4 years (range: 0.5-16.9 years) n = 36 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: 7.4 years (range: 0.5-16.9 years) Population Size: 36 Sources: |
| Chills | 10% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Sweating | 12% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Infection | 13% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Vomiting | 13% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Anorexia | 14% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Sepsis | 15% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Anemia | 25% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Leukopenia | 41% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Diarrhea | 44% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Fever | 48% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Pruritus | 5% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Thrombocytopenia | 6% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Catheter sepsis | 8% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Catheter infection | 9% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
| Neuropathy | 9% | 5 mg/kg 1 times / day multiple, intravenous Recommended Dose: 5 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 5 mg/kg, 1 times / day Sources: |
unhealthy, adult n = 179 Health Status: unhealthy Condition: CMV retinitis in HIV infection Age Group: adult Sex: M+F Population Size: 179 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Oral ganciclovir and pharmacokinetics of valganciclovir in liver transplant recipients. | 1999 |
|
| Outcome of lamivudine resistant hepatitis B virus infection in the liver transplant recipient. | 2000 Jan |
|
| Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
|
| Indolocarbazoles exhibit strong antiviral activity against human cytomegalovirus and are potent inhibitors of the pUL97 protein kinase. | 2000 Oct |
|
| Anti-(herpes simplex virus) activity of 4'-thio-2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes. | 2000 Oct 15 |
|
| Guanosine analogues as anti-herpesvirus agents. | 2000 Oct-Dec |
|
| Naphthalene carboxamides as inhibitors of human cytomegalovirus DNA polymerase. | 2000 Sep 18 |
|
| Prophylaxis against herpesvirus infections in transplant recipients. | 2001 |
|
| Pharmacokinetics of the ganciclovir implant in the silicone-filled eye. | 2001 |
|
| Suicide gene therapy for human oral squamous cell carcinoma cell lines with adeno-associated virus vector. | 2001 Apr |
|
| Intravitreal pharmacokinetics and retinal concentrations of ganciclovir and foscarnet after intravitreal administration in rabbits. | 2001 Apr |
|
| Suspension of anticytomegalovirus maintenance therapy following immune recovery due to highly active antiretroviral therapy. | 2001 Apr |
|
| Protection from lethal murine graft-versus-host disease without compromise of alloengraftment using transgenic donor T cells expressing a thymidine kinase suicide gene. | 2001 Apr 15 |
|
| Immune-dependent distant bystander effect after adenovirus-mediated suicide gene transfer in a rat model of liver colorectal metastasis. | 2001 Feb |
|
| Failure of cidofovir to reduce CMV-antigenemia in a child transplanted from a matched unrelated donor. | 2001 Feb |
|
| Construction of gene therapy vectors targeting thyroid cells: enhancement of activity and specificity with histone deacetylase inhibitors and agents modulating the cyclic adenosine 3',5'-monophosphate pathway and demonstration of activity in follicular and anaplastic thyroid carcinoma cells. | 2001 Feb |
|
| Rising pp65 antigenemia during preemptive anticytomegalovirus therapy after allogeneic hematopoietic stem cell transplantation: risk factors, correlation with DNA load, and outcomes. | 2001 Feb 15 |
|
| Preemptive ganciclovir for CMV viremia in liver transplantation. | 2001 Feb-Mar |
|
| Prophylactic antiviral therapy in CMV high-risk liver transplant recipients. | 2001 Feb-Mar |
|
| Ganciclovir prophylaxis for cytomegalovirus infection in simultaneous kidney-pancreas transplant recipients receiving tacrolimus, mycophenolate mofetil, and prednisone. | 2001 Feb-Mar |
|
| CMV in kidney transplants in the tacrolimus-mycophenolate era. | 2001 Feb-Mar |
|
| Rat glioma cell death induced by cationic liposome-mediated transfer of the herpes simplex virus thymidine kinase gene followed by ganciclovir treatment. | 2001 Jan |
|
| Targeting the replication of adenovirus to p53-defective thyroid carcinoma with a p53-regulated Cre/loxP system. | 2001 Jan |
|
| Epstein-Barr virus encephalitis in a renal allograft recipient diagnosed by polymerase chain reaction on cerebrospinal fluid and successfully treated with ganciclovir. | 2001 Jan |
|
| Recurrent disseminated herpes zoster and cytomegalic perianal ulcer: a case report and review of the literature. | 2001 Jan |
|
| Imaging in vivo herpes simplex virus thymidine kinase gene transfer to tumour-bearing rodents using positron emission tomography and. | 2001 Jan |
|
| [Gene therapy for colorectal cancer]. | 2001 Jan |
|
| [Perspectives on postgenome medicine: Gene therapy for brain tumors]. | 2001 Jan |
|
| In vitro effects of antiviral agents on human keratocytes. | 2001 Jan |
|
| Management of complications associated with totally implantable ports in patients with AIDS. | 2001 Jan |
|
| Cytomegalovirus hemorrhagic gastritis. | 2001 Jan |
|
| Cytomegalovirus infection and non-neutropenic fever after autologous stem cell transplantation: high rates of reactivation in patients with multiple myeloma and lymphoma. | 2001 Jan |
|
| Gene therapy for hepatocellular carcinoma based on tumour-selective suicide gene expression using the alpha-fetoprotein (AFP) enhancer and a housekeeping gene promoter. | 2001 Jan |
|
| Molecular mechanism for ganciclovir resistance in human T lymphocytes transduced with retroviral vectors carrying the herpes simplex virus thymidine kinase gene. | 2001 Jan 1 |
|
| Administration of herpes simplex-thymidine kinase-expressing donor T cells with a T-cell-depleted allogeneic marrow graft. | 2001 Jan 1 |
|
| Disseminated cytomegalovirus disease in hosts without acquired immunodeficiency syndrome and without an organ transplant. | 2001 Jan 15 |
|
| Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation. | 2001 Jan 15 |
|
| Mutations conferring ganciclovir resistance in a cohort of patients with acquired immunodeficiency syndrome and cytomegalovirus retinitis. | 2001 Jan 15 |
|
| The real danger of lamivudine-resistant hepatitis B virus infection in the immunocompromised host. | 2001 Mar |
|
| High-dose intravitreal ganciclovir and foscarnet for cytomegalovirus retinitis. | 2001 Mar |
|
| New developments in the management of cytomegalovirus infection and disease after renal transplantation. | 2001 Mar |
|
| Protease pretreatment increases the efficacy of adenovirus-mediated gene therapy for the treatment of an experimental glioblastoma model. | 2001 Mar 1 |
|
| Expression of herpes simplex virus-thymidine kinase gene controlled by a promoter region of the midkine gene confers selective cytotoxicity to ganciclovir in human carcinoma cells. | 2001 Mar 1 |
|
| Preemptive therapy versus universal prophylaxis with ganciclovir for cytomegalovirus in solid organ transplant recipients. | 2001 Mar 1 |
|
| Adenovirus-mediated gene therapy specific for small cell lung cancer cells using a Myc-Max binding motif. | 2001 Mar 15 |
|
| Prophylaxis for CMV should not now replace pre-emptive therapy in solid organ transplantation. | 2001 Mar-Apr |
|
| Reactivity of valganciclovir in aqueous solution. | 2005 Oct |
|
| The Role of Antiviral Prophylaxis for the Prevention of Epstein-Barr Virus-Associated Posttransplant Lymphoproliferative Disease in Solid Organ Transplant Recipients: A Systematic Review. | 2017 Mar |
|
| A 42-Year-Old Woman With Anemia, Shock, and Ischemic Stroke After Lung Transplantation. | 2017 Mar |
|
| Top 1% of Inpatients Administered Antimicrobial Agents Comprising 50% of Expenditures: A Descriptive Study and Opportunities for Stewardship Intervention. | 2017 Mar |
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175865-67-5
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135565169
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FR5B7CU4CF
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DTXSID60170036
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
